Synthesis and coordination chemistry of thiophenol-based heterodonor ligands containing P,S, As,S and P,SAs donor atoms

Imola Sárosi, Luminiţa Silaghi-Dumitrescu, Evamarie Hey-Hawkins

Abstract


This review article describes the synthesis and coordination chemistry of three types of thiophenol-based heterodonor ligands containing tertiary phosphine and/or arsine groups in combination with sulfur. Phenylthio(diphenyl)phosphine and -arsine ligands, EPh2(SPh) (E = P, As), incorporate an E–S bond in their structures. Upon reaction with different metal carbonyls, metal-mediated cleavage of the E–S bonds of these ligands has been observed, leading to a variety of sulfur- and phosphorus- or arsenic-containing metallacycles. The structurally isomeric phosphino- and arsinoarylthiols HSC6H4-2-EPh2 (ESH) combine a phosphine or arsine centre with a thiol functionality, which is usually deprotonated on coordination. These compounds have been shown to be very versatile ligands that form stable complexes with a wide range of transition metals. The heterotopic ligand 1-Ph2AsSC6H4-2-PPh2 (P,SAs) not only combines the properties of phenylthio(diphenyl)arsine and 2-diphenylphosphanylbenzenethiol by incorporating all three donor atoms in its structure, but also allows the effect of the PPh2 group in the ortho position on the cleavage of the As–S bond to be studied.


Keywords


P,S ligands, As,S ligands, P,SAs ligands, synthetic methods, transition metal complexes

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References


P. Braunstein, F. Naud, Hemilability of Hybrid Ligands and the Coordination Chemistry of Oxazoline-Based Systems, Angew. Chem. Int. Ed., 40, 680–699 (2001); P. Braunstein, F. Naud, Hemilabilität von Hybridliganden und die Koordinationschemie von Oxazolinliganden, Angew. Chem., 113, 702–722 (2001).

C.S. Slone, D.A. Weinberger, C.A. Mirkin, The Transition Metal Coordination Chemistry of Hemilabile Ligands, in: Prog. Inorg. Chem., John Wiley & Sons, Inc., 2007, pp. 233–350.

M. Bassetti, Kinetic Evaluation of Ligand Hemilability in Transition Metal Complexes, Eur. J. Inorg. Chem., 4473–4482 (2006).

A. Bader, E. Lindner, Coordination chemistry and catalysis with hemilabile oxygen-phosphorus ligands, Coord. Chem. Rev., 108, 27–110 (1991).

J.R. Dilworth, N. Wheatley, The preparation and coordination chemistry of phosphorus–sulfur donor ligands, Coord. Chem. Rev., 199, 89–158 (2000).

J.J. Schneider, Hemilabile Liganden in Katalyse und Komplexchemie, Nachr. Chem., 48, 614–620 (2000).

K.N. Gavrilov, A.I. Polosukhin, Chiral P,N-bidentate ligands in coordination chemistry and organic catalysis involving rhodium and palladium, Russian Chemical Reviews, 69, 661–682 (2000).

G. Delapierre, G. Buono, P,N chiral ligands: Diversity and new advances, Actual. Chim., 3–11 (2003).

J.C. Jeffrey, T.B. Rauchfuss, Metal complexes of hemilabile ligands. Reactivity and structure of dichlorobis(o-(diphenylphosphino)anisole)ruthenium(II), Inorg. Chem., 18, 2658–2666 (1979).

P. Braunstein, D. Matt, F. Mathey, D. Thavard, Functional phosphines: a new synthesis of diphenylphosphinoacetonitrile and ethyl diphenylphosphinoacetate; some of their complexes with iron(0), gold(I), nickel(II), palladium(II), platinum(II), rhodium(III), and iridium(III). Stereodynamic behavior, J. Chem. Res. (S), 232–233 (1978).

P. Braunstein, D. Matt, F. Mathey, D. Thavard, Functional phosphines: a new synthesis of diphenylphosphinoacetonitrile and ethyl diphenylphosphinoacetate; some of their complexes with iron(0), gold(I), nickel(II), palladium(II), platinum(II), rhodium(III), and iridium(III). Stereodynamic behavior, J. Chem. Res. (M), 3041 (1978).

P. Braunstein, Functional ligands and complexes for new structures, homogeneous catalysts and nanomaterials, J. Organomet. Chem., 689, 3953–3967 (2004).

P. Braunstein, M. Knorr, C. Stern, Bimetallic silicon chemistry: New opportunities in coordination and organometallic chemistry, Coord. Chem. Rev., 178–180, Part 2, 903–965 (1998).

N. Lugan, F. Laurent, G. Lavigne, T.P. Newcomb, E.W. Liimatta, J.J. Bonnet, Nucleophilic activation of triruthenium carbonyl complexes by semi-labile ancillary ligands. Cluster assisted codimerization of alkynes and ethylene to give 1,2-disubstituted-1,3-butadienes, J. Am. Chem. Soc., 112, 8607–8609 (1990).

N. Lugan, F. Laurent, G. Lavigne, T.P. Newcomb, E.W. Liimatta, J.J. Bonnet, Activation of triruthenium carbonyl complexes by incorporation of hemilabile ancillary ligands containing alkoxo, amido, or thiolato groups. Generation of a reactive alkenyl complex, Organometallics, 11, 1351–1363 (1992).

M. Yuki, Y. Miyake, Y. Nishibayashi, Preparation of Thiolate-Bridged Dinuclear Ruthenium Complexes Bearing a Phosphine Ligand and Application to Propargylic Reduction of Propargylic Alcohols with 2-Propanol, Organometallics, 29, 5994–6001 (2010).

L.-P. He, M. Hong, B.-X. Li, J.-Y. Liu, Y.-S. Li, Ethylene/hexene living copolymerization and ethylene/methyl 10-undecenoate copolymerization by titanium complexes bearing phenoxy-phosphine or thiophenoxy-phosphine ligands, Polymer, 51, 4336–4339 (2010).

P. Fernández, A. Sousa-Pedrares, J. Romero, M.L. Durán, A. Sousa, P. Pérez-Lourido, J.A. García-Vázquez, Synthesis and Structural Characterization of Cobalt, Nickel and Copper Phosphanylthiolato Complexes, Eur. J. Inorg. Chem., 2010, 814–823 (2010).

S. Ye, F. Neese, A. Ozarowski, D. Smirnov, J. Krzystek, J. Telser, J.-H. Liao, C.-H. Hung, W.-C. Chu, Y.-F. Tsai, R.-C. Wang, K.-Y. Chen, H.-F. Hsu, Family of V(III)-Tristhiolato Complexes Relevant to Functional Models of Vanadium Nitrogenase: Synthesis and Electronic Structure Investigations by Means of High-Frequency and -Field Electron Paramagnetic Resonance Coupled to Quantum Chemical Computations, Inorg. Chem., 49, 977–988 (2009).

A.-M. Vălean, S. Gomez-Ruiz, P. Lönnecke, I. Silaghi-Dumitrescu, L. Silaghi-Dumitrescu, E. Hey-Hawkins, Stabilisation of an inorganic digallane by the phosphinobisthiolato P,S,S pincer ligand PPh(2-SC6H4)2, New J. Chem., 33, 1771–1779 (2009).

P.B. Kraikivskii, M. Frey, H.A. Bennour, A. Gembus, R. Hauptmann, I. Svoboda, H. Fuess, V.V. Saraev, H.-F. Klein, Syntheses and properties of molecular nickel(II) hydride, methyl, and nickel(I) complexes supported by trimethylphosphane and (2-diphenylphosphanyl)thiophenolato and -naphtholato ligands, J. Organomet. Chem., 694, 1869–1876 (2009).

A.M. Vălean, S. Gómez-Ruiz, P. Lönnecke, I. Silaghi-Dumitrescu, L.a. Silaghi-Dumitrescu, E. Hey-Hawkins, When Arsine Makes the Difference: Chelating Phosphino and Bridging Arsinoarylthiolato Gallium Complexes, Inorg. Chem., 47, 11284–11293 (2008).

T.-W. Chiou, W.-F. Liaw, Mononuclear Nickel(III) Complexes [NiIII(OR)(P(C6H3-3-SiMe3-2-S)3)]− (R = Me, Ph) Containing the Terminal Alkoxide Ligand: Relevance to the Nickel Site of Oxidized-Form [NiFe] Hydrogenases, Inorg. Chem., 47, 7908–7913 (2008).

V. Gómez-Benítez, R.A. Toscano, D. Morales-Morales, Synthesis and characterization of [Pd{PhP(C6H4-2-SCH2Cl)(C6H4-2-S)}(Ph2PCH2CH2PPh2)]Cl: An example of hemilability and dichloromethane activation, Inorg. Chem. Commun., 10, 1–6 (2007).

L. She, X. Li, H. Sun, J. Ding, M. Frey, H.-F. Klein, Insertion of Alkynes into Ni−H Bonds: Synthesis of Novel Vinyl Nickel(II) and Dinuclear Vinyl Nickel(II) Complexes Containing a [P, S]-Ligand, Organometallics, 26, 566–570 (2007).

C.-M. Lee, Y.-L. Chuang, C.-Y. Chiang, G.-H. Lee, W.-F. Liaw, Mononuclear Ni(III) Complexes [NiIII(L)(P(C6H3-3-SiMe3-2-S)3)]0/1– (L = Thiolate, Selenolate, CH2CN, Cl, PPh3): Relevance to the Nickel Site of [NiFe] Hydrogenases, Inorg. Chem., 45, 10895–10904 (2006).

W.-C. Chu, C.-C. Wu, H.-F. Hsu, Catalytic Reduction of Hydrazine to Ammonia by a Vanadium Thiolate Complex, Inorg. Chem., 45, 3164–3166 (2006).

M. Gorol, H.W. Roesky, M. Noltemeyer, H.-G. Schmidt, (η5-Pentamethylcyclopentadienyl)iridium(III) Complexes with η2-N,O and η2-P,S Ligands, Eur. J. Inorg. Chem., 4840–4844 (2005).

J.A. Cabeza, M.A. Martínez-García, V. Riera, D. Ardura, S. García-Granda, Reactivity of 2-(Diphenylphosphanyl)thiophenol (HSC6H4PPh2) with Ruthenium and Osmium Carbonyl Complexes; Breaking of HSC6H4PPh2 into Sulfide, Phenyl and Diphenylphosphanyl Ligands on a Triruthenium Cluster, Eur. J. Inorg. Chem., 2000, 499–503 (2000).

J. Mason, Multinuclear NMR, Springer US, 1987.

S.B. Wild, Optically Active Arsines: Preparation, Uses and Chiroptical Properties, in: Organic Arsenic, Antimony and Bismuth Compounds (1994), John Wiley & Sons, Ltd, 2004, pp. 89–152.

V. Farina, B. Krishnan, Large rate accelerations in the stille reaction with tri-2-furylphosphine and triphenylarsine as palladium ligands: mechanistic and synthetic implications, J. Am. Chem. Soc., 113, 9585–9595 (1991).

C. Amatore, A.A. Bahsoun, A. Jutand, G. Meyer, N. Ndedi, L. Ricard, Mechanism of the Stille Reaction Catalyzed by Palladium Ligated to Arsine Ligand: PhPdI(AsPh3)(DMF) Is the Species Reacting with Vinylstannane in DMF, J. Am. Chem. Soc., 125, 4212–4222 (2003)..

C.R. Johnson, M.P. Braun, A two-step, three-component synthesis of PGE1: utilization of -iodoenones in Pd(0)-catalyzed cross-couplings of organoboranes, J. Am. Chem. Soc., 115, 11014–11015 (1993).

R.B. Bedford, C.S.J. Cazin, S.J. Coles, T. Gelbrich, M.B. Hursthouse, V.J.M. Scordia, Phosphine and arsine adducts of N-donor palladacycles as catalysts in the Suzuki coupling of aryl bromides, Dalton Trans., 3350–3356 (2003).

L.A. van der Veen, P.K. Keeven, P.C.J. Kamer, P.W.N.M. van Leeuwen, Novel arsine ligands for selective hydroformylation of alk-1-enes employing platinum/tin catalysts, Chem. Commun., 333–334 (2000).

R.A. Baber, S. Collard, M. Hooper, A.G. Orpen, P.G. Pringle, M.J. Wilkinson, R.L. Wingad, Bulky triarylarsines are effective ligands for palladium catalysed Heck olefination, Dalton Trans., 1491–1498 (2005).

S. Ceccarelli, U. Piarulli, C. Gennari, Effect of Ligands and Additives on the Palladium-Promoted Carbonylative Coupling of Vinyl Stannanes and Electron-Poor Enol Triflates, J. Org. Chem., 65, 6254–6256 (2000).

W.-M. Dai, A. Wu, H. Wu, Asymmetric Wittig reactions of chiral arsonium ylides. Part 3: Reversal of stereochemistry caused by metal cation in enantioselective olefination of 4-substituted cyclohexanones using a C2-symmetric chiral arsine, Tetrahedron: Asymmetry, 13, 2187–2191 (2002).

E.S. Raper, Complexes of heterocyclic thione donors, Coord. Chem. Rev., 61, 115-184 (1985).

P.J. Blower, J.R. Dilworth, Thiolato-complexes of the transition metals, Coord. Chem. Rev., 76, 121–185 (1987).

E.S. Raper, Complexes of heterocyclic thionates. Part 1. Complexes of monodentate and chelating ligands, Coord. Chem. Rev., 153, 199–255 (1996).

E.S. Raper, Complexes of heterocyclic thionates Part 2: complexes of bridging ligands, Coord. Chem. Rev., 165, 475–567 (1997).

H. Fritzsche, U. Hasserodt, F. Korte, A New Method for the Formation of P–P Bonds, Angew. Chem., Int. Ed., 3, 64–64 (1964); H. Fritzsche, U. Hasserodt, F. Korte, Weiteres Verfahren zur Knüpfung von P–P-Bindungen, Angew. Chem., 75, 1205–1205 (1963).

R. Fusco, C.A. Peri, V. Corradini, Sulfur-containing arsenical fungicides, Montecatini, Patent: BE621008, (1963).

B.E. Job, R.A.N. McLean, D.T. Thompson, Binuclear metal carbonyls having both phosphorus and sulphur bridges, Chem. Commun. (London), 895–896 (1966).

R.A.N. McLean, Phenylthio- and phenylseleno-diphenyl phosphine, Inorganic and Nuclear Chemistry Letters, 5, 745–747 (1969).

S.C. Peake, R. Schmutzler, Phosphorus-fluorine chemistry. Part XXII. Alkylthio- and arylthio-substituted fluorophosphoranes, J. Chem. Soc. A, 1049–1054 (1970).

L. Horner, M. Jordan, Phosphororganische Verbindungen 90, Phosphorus Sulfur, 8, 215–219 (1980).

C.D. Hall, B.R. Tweedy, R. Kayhanian, J.R. Lloyd, The kinetics and mechanism of the reaction of tricoordinate phosphorus compounds with diaryl trisulfides, J. Chem. Soc., Perk. Trans. 2, 775–779 (1992).

V. Cadierno, M. Zablocka, B. Donnadieu, A. Igau, J.-P. Majoral, A. Skowronska, X−H (X=C, N, O, P, S) Bond Activations Induced by β-Heterosubstituted Zirconaindenes, Chem. Eur. J., 7, 221–229 (2001).

L.-B. Han, T.D. Tilley, Selective Homo- and Heterodehydrocouplings of Phosphines Catalyzed by Rhodium Phosphido Complexes, J. Am. Chem. Soc., 128, 13698–13699 (2006).

T.D. Sideris, P.V. Ioannou, Studies on the Air Oxidation of Some Arsenic(III) Compounds, Phosphorus Sulfur, 181, 751–762 (2006).

R.M. Bozorth, The Crystal Structures of The Cubic Forms of Arsenious and Antimonous Oxides, J. Am. Chem. Soc., 45, 1621–1627 (1923).

J. Kopf, K. Von Deuten, G. Klar, Crystal and molecule structure of 1,3,5,7-tetraarsa-2,4,6,8-tetraoxaadamantane, Inorg. Chim. Acta, 38, 67–69 (1980).

B.J. McKerley, K. Reinhardt, J.L. Mills, G.M. Reisner, J.D. Korp, I. Bernal, Synthesis and structure of an Organocyclotriarsinetrioxide, Inorg. Chim. Acta, 31, L411–L412 (1978).

I. Bernal, H. Brunner, W. Meier, H. Pfisterer, J. Wachter, M.L. Ziegler, Ligand Extrusion from the As4S4-Cage by [C5Me5(CO)2Mo]2: Formation of (C5Me5)2Mo2(CO)4(μ,η2-As2), C5Me5(CO)2Mo(η3-As3), and (C5Me5)2Mo2As2S3, Angew. Chem., Int. Ed., 23, 438–439 (1984); I. Bernal, H. Brunner, W. Meier, H. Pfisterer, J. Wachter, M.L. Ziegler, Ligandenerzeugung aus dem As4S4-Käfig durch [C5Me5(CO)2Mo]2: Bildung von (C5Me5)2Mo2(CO)4(μ,η2-As2), C5Me5(CO)2Mo(η3-As3) und (C5Me5)2Mo2As2S3, Angew. Chem., 96, 428–429 (1984)..

H. Brunner, H. Kauermann, B. Nuber, J. Wachter, M.L. Ziegler, Complex-Induced Fragmentation of As4S4: Stabilization of an As2S3 Ligand, Angew. Chem., Int. Ed., 25, 557-558 (1986); H. Brunner, H. Kauermann, B. Nuber, J. Wachter, M.L. Ziegler, Komplexinduzierter Abbau von As4S4: Stabilisierung eines As2S3 -Liganden, Angew. Chem., 98, 551–552 (1986)..

H. Brunner, L. Poll, J. Wachter, B. Nuber, New As-S Cage Structures with Organometallic Components Formed by Complex-Induced Realgar Fragmentation, Angew. Chem., Int. Ed., 32, 1627-1628 (1993); H. Brunner, B. Nuber, L. Poll, J. Wachter, Neue As-S-Käfigstrukturen mit metallorganischen Komponenten durch komplexinduzierten Realgar-Abbau, Angew. Chem., 105, 1699–1701 (1993).

H. Brunner, L. Poll, J. Wachter, B. Nuber, Neue FeAsS-Käfigstrukturen aus [Cp+Fe(CO)2]2 (Cp+ = C5Me4Et) und Realgar, J. Organomet. Chem., 471, 117–122 (1994).

H. Brunner, L. Poll, J. Wachter, New insights into the cage fragmentation of As4S4 and As4S3 by their interaction with (C5Me4Et)2Fe2(CO)4, Polyhedron, 15, 573–576 (1996).

H. Brunner, H. Kauermann, L. Poll, B. Nuber, J. Wachter, The Reaction of As4Sn (n = 3, 4) and As2S3 with (C5Me4R)2Co2(CO)2 (R = Me, Et): Fragmentation and Reassembling of Main-Group Ligands by Organometallic Complexes, Chem. Ber., 129, 657–662 (1996).

G. Le Borgne, R. Mathieu, Structural study of iron carbonyl derivatives V. Synthesis and crystal and molecular structure of μ-(SC6H5)-μ-(P(C6H5)2)Fe2(CO)6, J. Organomet. Chem., 208, 201–212 (1981).

G. Conole, J.E. Davies, J.D. King, M.J. Mays, M. McPartlin, H.R. Powell, P.R. Raithby, Reactions of thioarsines with metal carbonyls: synthesis and structural characterisation of [Fe2(CO)6(μ-AsMe2)(μ-SPh)], [Fe2Cp2(CO)2(μ-AsPh2)(μ-SPh)], [Mn2(CO)8(μ-AsPh2)(μ-SPh)] and [Co3(μ3-S)(μ-AsPh2)(CO)6AsPh3], J. Organomet. Chem., 585, 141–149 (1999).

J.A. Adeleke, Y.W. Chen, L.K. Liu, Preparation and crystal structures of iron complexes syn-[(μ-SPh)Fe(CO)3]2, (C5H4SPh)2Fe, (C5H5)Fe(C5H4SPh), and (C5H4SPh)Fe(C5H4PPh2), Organometallics, 11, 2543–2550 (1992).

A.J. Edwards, A. Martin, M.J. Mays, P.R. Raithby, G.A. Solan, Interchange of SPh and PPh2 groups at a dicobalt centre: crystal and molecular structures of [Co2(μ-PPh2){μ-SPhC(O)CHCH}(CO)4] and [Co2(μ-SPh){μ-PPh2CHCHC(O)}(CO)2{P(OMe)3}2], J. Chem. Soc., Chem. Commun., 1416–1418 (1992).

G. Conole, M. Kessler, M.J. Mays, G.E. Pateman, G.A. Solan, Labile SR′C(O)CRCH-bridged dicobalt complexes;synthesis structures 13CO labelling studies, Polyhedron, 17, 2993–3004 (1998).

A.J. Edwards, A. Martian, M.J. Mays, D. Nazar, P.R. Raithby, G.A. Solan, Synthesis and reactions with alkynes of complexes containing both phosphorus and sulfur bridging ligands: crystal and molecular structures of [Mn2(μ-PPh2)(μ-SPh)(CO)8], [Co3(μ3-S)(μ-PPh2)(CO)6(PPh3)] and [Co3(μ3-S)(μ-PPh2CHCPh)(CO)6(PPh3)], J. Chem. Soc., Dalton Trans., 355–363 (1993).

A. Martin, M.J. Mays, P.R. Raithby, G.A. Solan, Reactions of the heteronuclear alkyne-bridged cobalt-molybdenum complex [(OC)3Co{μ-C2(CO2Me)2}Mo(CO)2(η5-C5H5)] with PPh2H, P2Ph4 and PPh2(SPh), J. Chem. Soc., Dalton Trans., 1431–1439 (1993).

S.L. Ingham, M.J. Mays, P.R. Raithby, G.A. Solan, B.V. Sundavadra, G. Conole, M. Kessler, Phosphorus-sulfur bond cleavage at a mixed-metal centre; reaction of [(OC)3Co(μ-PHCCH)Mo(CO)2(η5-C5H5)] with PPh2(SPh), J. Chem. Soc., Dalton Trans., 3607–3614 (1994).

J. D. King, M. J. Mays, G. E. Pateman, P. R. Raithby, M. A. Rennie, G. A. Solan, N. Choi, G. Conole, M. McPartlin, The formation and transformation of metallacycles containing phosphorus or sulfur on molybdenum- or tungsten-cobalt mixed-metal backbones, J. Chem. Soc., Dalton Trans., 4447–4456 (1999).

E. Block, G. Ofori-Okai, J. Zubieta, 2-Phosphino- and 2-phosphinylbenzenethiols: new ligand types, J. Am. Chem. Soc., 111, 2327–2329 (1989).

A. Hildebrand, I. Sárosi, P. Lönnecke, L. Silaghi-Dumitrescu, M.B. Sárosi, I. Silaghi-Dumitrescu, E. Hey-Hawkins, Heteropolytopic Arsanylarylthiolato Ligands: Cis–Trans Isomerism of Nickel(II), Palladium(II), and Platinum(II) Complexes of 1-AsPh2-2-SHC6H4, Inorg. Chem., 51, 7125–7133 (2012).

S.E. Livingstone, T.N. Lockyer, Metal complexes of two new sulphur-phosphorus chelating agents, Inorg. Nucl. Chem. Lett., 3, 35–38 (1967).

G.D. Figuly, C.K. Loop, J.C. Martin, Directed ortho-lithiation of lithium thiophenolate. New methodology for the preparation of ortho-substituted thiophenols and related compounds, J. Am. Chem. Soc., 111, 654–658 (1989).

E. Block, V. Eswarakrishnan, M. Gernon, G. Ofori-Okai, C. Saha, K. Tang, J. Zubieta, o-Lithiothiophenol equivalents. Generation, reactions and applications in synthesis of hindered thiolate ligands, J. Am. Chem. Soc., 111, 658–665 (1989).

K. Smith, C.M. Lindsay, G.J. Pritchard, Directed lithiation of arenethiols, J. Am. Chem. Soc., 111, 665–669 (1989).

P. Beak, R.A. Brown, The tertiary amide as an effective director of ortho lithiation, J. Org. Chem., 47, 34–46 (1982).

P. Beak, V. Snieckus, Directed lithiation of aromatic tertiary amides: an evolving synthetic methodology for polysubstituted aromatics, Acc. Chem. Res., 15, 306–312 (1982).

V. Snieckus, Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics, Chem. Rev., 90, 879–933 (1990).

C.G. Hartung, V. Snieckus, The Directed ortho Metalation Reaction – A Point of Departure for New Synthetic Aromatic Chemistry, in: Modern Arene Chemistry, D. Astruc (Ed.), Wiley-VCH Verlag GmbH & Co. KGaA, 2004, pp. 330–367.

A. Wheatley, The Directed Lithiation of Benzenoid Aromatic Systems, Eur. J. Inorg. Chem., 2003, 3291–3303 (2003).

B. J. Wakefield, The Chemistry of Organolithium Compounds, Pergamon, Oxford, UK, 1974.

M. Gray, M. Tinkl, V. Sniekus, Lithium, in: Comprehensive Organometallic Chemistry II, G. Wilkinson, F. G. A. Stone, E. Abel (Eds.), Pergamon, Oxford, UK, 1991.

A. Streitwieser, Carbanion ion pairs and triplets, Acc. Chem. Res., 17, 353–357 (1984).

D. Kost, J. Klein, A. Streitwieser, G.W. Schriver, Ab initio calculations of dilithiopropenes, Proc. Natl. Acad. Sci. U.S.A., 79, 3922–3926 (1982).

A. Hildebrand, P. Lönnecke, I. Silaghi-Dumitrescu, L. Silaghi-Dumitrescu, E. Hey-Hawkins, Co-complexes of ortho-dilithiated thiophenol or 2-trimethylsilylthiophenol with lithiated TMEDA molecules: synthesis, crystal structures and theoretical studies (TMEDA = N,N,N',N'-tetramethylethylenediamine), Dalton Trans., 967–974 (2006).

S.E. Livingstone, 858. Metallic complexes of dimethyl-o-methylthiophenylarsine. Part I. Complexes of nickel and palladium, J. Chem. Soc., 4222–4226 (1958).

B. Chiswell, S.E. Livingstone, 219. Metallic complexes of dimethyl-o-(methylthio)phenylarsine. Part IV. Complexes of platinum, J. Chem. Soc., 1071–1074 (1960).

N.C. Stephenson, The crystal structure of di-iododi-(o-phenylenebisdimethylarsine) platinum(II) Pt(C6H4[As(CH3)2]2)2I2, J. Inorg. Nucl. Chem., 24, 791–795 (1962).

V.F. Duckworth, N.C. Stephenson, Crystal structure of diiodobis(o-phenylenebis(dimethylarsine))gold(III) iodide-a discrete six-coordinate cationic complex of gold(III), Inorg. Chem., 8, 1661–1664 (1969).

J.P. Beale, N.C. Stephenson, The crystal and molecular structure of diiodobis(dimethyl-o-methylthiophenylarsine)palladium(II), Acta Cryst. B, 26, 1655–1661 (1970).

J.P. Beale, N.C. Stephenson, The crystal and molecular structure of bis(dimethyl-o-thiolophenylarsine)platinum(II), Acta Cryst. B, 27, 73–80 (1971).

E.M. Miller, B.L. Shaw, Kinetic and other studies on oxidative addition reactions of iridium phosphine complexes of the type trans-[IrCl(CO)(PMe2R)2](R = Ph, o-MeO∙C6H4, or p-MeO∙C6H4), J. Chem. Soc., Dalton Trans., 480–485 (1974).

L.F. Lindoy, S.E. Livingstone, T.N. Lockyer, S-dealkylation and S-alkylation reactions of metal chelates of sulfur ligands, Inorg. Chem., 6, 652–656 (1967).

G. Dyer, M.O. Workman, D.W. Meek, Palladium(II) complexes with polydentate phosphorus-sulfur ligands, Inorg. Chem., 6, 1404–1407 (1967).

L. Lindoy, S. Livingstone, T. Lockyer, Sulphur-nitrogen chelating agents. IV. Metal complexes of o-methylthioaniline, Aust. J. Chem., 20, 471–478 (1967).

T. Lockyer, S-Dealkylation reactions of palladium(II) complexes of some phosphorus-sulphur and arsenic-sulphur chelates, Aust. J. Chem., 27, 259–267 (1974).

S.K. Harbron, S.J. Higgins, E.G. Hope, T. Kemmitt, W. Levason, Coordination chemistry of higher oxidation states. Part 24. Palladium(IV) and nickel(III) complexes of hybrid thio- and seleno-ether ligands, Inorg. Chim. Acta, 130, 43–47 (1987).

M.G. Fitzpatrick, L.R. Hanton, W. Henderson, P.E. Kneebone, E.G. Levy, L.J. McCaffrey, D.A. McMorran, Application of electrospray mass spectrometry to the characterisation of tertiary arsine ligands, Inorg. Chim. Acta, 281, 101–110 (1998).

W.S. Tsang, D.W. Meek, A. Wojcicki, Seven-coordinate carbonyl complexes of molybdenum(II) and tungsten(II), Inorg. Chem., 7, 1263–1268 (1968).

E. Block, H. Kang, G. Oforiokai, J. Zubieta, Coordination chemistry of molybdenum with novel thiolate ligands. The crystal and molecular structures of a binuclear complex with a Mo–Mo triple bond [Mo2(SC6H4-o-PPh2)3Cl3] and of [Mo(SC6H3-2-SiMe3-6-P(O)Ph2)2Cl2], a species exhibiting [MoO2S2Cl2] coordination, Inorg. Chim. Acta, 166, 155–157 (1989).

C. Bolzati, F. Refosco, F. Tisato, G. Bandoli, A. Dolmella, Novel TcP3X3 (X = S, O) cores in Tc(III) chemistry, Inorg. Chim. Acta, 201, 7–10 (1992).

J. R. Dilworth, A. J. Huston, S. Morton, M. Harman, M. B. Hursthouse, J. Zubieta, C. M. Archer, J. D. Kelly, Polyhedron, 1992, 11, 2151–2155

C. Bolzati, A. Boschi, L. Uccelli, E. Malago, G. Bandoli, F. Tisato, F. Refosco, R. Pasqualini, A. Duatti, Inorg. Chem. 1999, 38, 4473–4479

J.R. Dilworth, A.J. Hutson, S. Morton, M. Harman, M.B. Hursthouse, J. Zubieta, C.M. Archer, J.D. Kelly, The preparation and electrochemistry of technetium and rhenium complexes of 2-(diphenylphosphino)benzenethiol. The crystal and molecular structures of [Re(2-Ph2PC6H4S)3] and [Tc(2-Ph2PC6H4S)3], Polyhedron, 11, 2151–2155 (1992).

P. Pérez-Lourido, J. Romero, J.A. García-Vázquez, A. Sousa, K.P. Maresca, J. Zubieta, Synthesis and Characterization of Rhenium(III) Organohydrazide Compounds. Crystal and Molecular Structures of [ReCl(PPh3)2(NHNC5H4N)(HNNC5H4N)]Cl2, [Re{2-(Ph2P)C6H4S}{2-(Ph2PO)C6H4S}(NNC5H4N)(HNNC5H4N)], and [Re{2-(Ph2P)C6H4S}2(NNC5H4N)], Inorg. Chem., 38, 1511–1519 (1999).

P. Perez-Lourido, J. Romero, J. Garcia-Vazquez, A. Sousa, K.P. Maresca, D.J. Rose, J. Zubieta, Synthesis and Characterization of Rhenium Phosphinothiolate Complexes. Crystal and Molecular Structures of [HNEt3][Re{P(C6H4S)3}2], [ReOCl{OP(C6H5)2(C6H4S)}{(P(C6H5)2(C6H4S)}], [Re2O5{P(C6H5)2(C6H4S)}2], and [ReOCl{OP(C6H5)2(2-SC6H3-3-SiMe3)}2], Inorg. Chem., 37, 3331–3336 (1998).

P. Pérez-Lourido, J. Romero, J.A. García-Vázquez, J. Castro, A. Sousa, L. Cooper, J.R. Dilworth, R.L. Richards, Y. Zheng, J.A. Zubieta, Synthesis and characterisation of iron and cobalt complexes with phosphinothiolate ligands, Inorg. Chim. Acta, 356, 193–202 (2003).

H.-F. Klein, M. Frey, S. Mao, Steering of Configuration by (2-Phosphanyl)phenolato Ligands in Trimethylphosphane Iron Complexes, Z. Anorg. Allg. Chem., 631, 1516–1523 (2005).

J. Dilworth, Y. Zheng, S. Lu, Q. Wu, Preparation and characterization of a novel asymmetrically oxidized complex of 2-(diphenylphosphino)-benzenethiol with ruthenium. The crystal and molecular structure of [Ru(2-Ph2PC6H4S)•(2-Ph2PC6H4S−OH)(2-Ph2PC6H4SO2)]•1/2H2O, Transition Met. Chem., 17, 364–368 (1992).

P. Pérez-Lourido, J. Romero, J.A. García-Vázquez, A. Sousa, J. Zubieta, K. Maresca, Synthesis and characterisation of cobalt and nickel compounds with phosphinothiol ligands. Crystal and molecular structures of [Co{2-(Ph2P)-6-(Me3Si)C6H3S)}3], [Ni{2-(Ph2P)-6-(Me3Si)C6H3S)}2] and [Co{2-(Ph2PO)-6-(Me3Si)C6H3S}2], Polyhedron, 17, 4457–4464 (1998).

H. Sun, L. She, S. Fang, X. Li, Reaction of acyl(hydrido)cobalt(III) complexes with (2-diphenylphosphanyl)thiophenol and the influence of chelating ligands containing hard/soft donor atoms on the stability of cobalt complexes, Polyhedron, 27, 854–860 (2008).

A. Hildebrand, M.B. Sárosi, P. Lönnecke, L. Silaghi-Dumitrescu, E. Hey-Hawkins, Unsymmetrical dinuclear rhodium complexes with arsanyl- and phosphanylarylthiolato ligands [Rh(μ-S-2-EPh2C6H4-κ2S,E)2Rh(cod)] (E = As, P), Rev. Roum. Chim., 55, 885–896 (2010).

J.R. Dilworth, J.R. Miller, N. Wheatley, M.J. Baker, J.G. Sunley, Novel catalysts for the carbonylation of methanol, J. Chem. Soc., Chem. Commun., 1579–1581 (1995).

M.J. Baker, J.R. Dilworth, J.G. Sunley, N. Wheatley, Process for the carbonylation of methanol or a reactive derivative thereof, Patent: EP632006A1, (1995).

L. Dahlenburg, K. Herbst, M. Kühnlein, Koordinationschemie funktioneller Phosphane. III. Rhodium- und Iridiumkomplexe mit 2-(Diphenylphosphanyl)phenolato- und 2-(Diphenylphosphanyl)thiophenolato-Liganden, Z. Anorg. Allg. Chem., 623, 250–258 (1997).

J.R. Dilworth, C. Lu, J.R. Miller, Y. Zheng, Complexes of 2- Diphenylphosphinobenzenethiol and 2-Diphenyl phosphino-6-trimethylsilylbenzenethiol with Rhodium and Iridium. Crystal and Molecular Structures of [IrCI2( Ph2PC6H4S)(PMePh2)2] and [Ir(Ph2PC6H4S)3]∙0.75CH2Cl2, J. Chem. Soc., Dalton Trans., 1957–1964 (1995).

A. Benefiel, D.M. Roundhill, W.C. Fultz, A.L. Rheingold, A Menschutkin type amine alkylation involving methyl transfer to benzylamine from palladium(II) chelate complexes of o-(diphenylphosphino)thioanisole, Inorg. Chem., 23, 3316–3324 (1984).

J. Real, E. Prat, A. Polo, Á. Álvarez-Larena, J.F. Piniella, Unexpected cis preference in palladium(II) bis(diphenylphosphinoarylthiolato) complexes. Crystal structure of cis-[Pd(PPh2(C6H4-2-S))2], Inorg. Chem. Commun., 3, 221–223 (2000).

D. Canseco-González, V. Gómez-Benı́tez, S. Hernández-Ortega, R.A. Toscano, D. Morales-Morales, Transmetallation reactions of [Sn(R)2(Ph2PC6H4-2-S)2] with metal complexes of the Group 10: Stereoselective synthesis of cis-[M(Ph2PC6H4-2-S)2] (M=Ni, Pd, Pt), J. Organomet. Chem., 679, 101–109 (2003).

J. Fierro-Arias, D. Morales-Morales, S. Hernandez-Ortega, cis-Bis[2-(diphenylphosphino)benzenethiolato-κ2P,S]palladium(II), Acta Cryst. E, 64, m1196 (2008).

A. Benefiel, D.M. Roundhill, Menschutkin type amine alkylations involving methyl transfer from platinum(II) chelate complexes of o-(diphenylphosphino)thiophenetole, Inorg. Chem., 25, 4027–4031 (1986).

J.R. Dilworth, A.J. Hutson, J. Zubieta, Q. Chen, The preparation and electrochemistry of gold(III), palladium(II) and platinum(II) complexes with 2-(diphenylphosphino)thiobenzene: X-ray crystal structure of [Au(Ph2PC6H4S)(Ph2][BPh4], Transition Met. Chem., 19, 61–64 (1994).

J.S. Kim, J.H. Reibenspies, M.Y. Darensbourg, Characteristics of Nickel(0), Nickel(I), and Nickel(II) in Phosphino Thioether Complexes: Molecular Structure and S-Dealkylation of (Ph2P(o-C6H4)SCH3)2Ni0, J. Am. Chem. Soc., 118, 4115–4123 (1996).

E. Block, G. Ofori-Okai, H. Kang, J. Zubieta, Complexes of Ni(II) with sterically-hindered thiolate ligands. Crystal structures of complexes with the [NiS2N2], [NiS2P2] and [NiS2O2] cores, Inorg. Chim. Acta, 188, 7–13 (1991).

A. Hildebrand, I. Sarosi, P. Lönnecke, L. Silaghi-Dumitrescu, M.B. Sarosi, I. Silaghi-Dumitrescu, E. Hey-Hawkins, Heteropolytopic phosphanylarylthiolato ligands: formation of cis isomers of nickel(II), palladium(II) and platinum(II) complexes with 1-P(Biph)-2-SHC6H4 (Biph = 1,1′-biphenyl-2,2′-diyl), Dalton Trans., 41, 7729–7736 (2012).

E.C. Constable, C.E. Housecroft, P. Kopecky, E. Schonhofer, J.A. Zampese, Restricting the geometrical relaxation in four-coordinate copper(I) complexes using face-to-face and edge-to-face -interactions, CrystEngComm, 13, 2742–2752 (2011).

[ ] P. Perez-Lourido, J.A. Garcia-Vazquez, J. Romero, P. Fernandez, A. Sousa-Pedrares, A. Sousa, Bis[2-(diphenylphosphinoyl)benzene] disulfide, Acta Cryst. C, 56, e101–e102 (2000).

P. Perez-Lourido, J.A. Garcia-Vazquez, J. Romero, A. Sousa, E. Block, K.P. Maresca, J. Zubieta, Synthesis and Structural Characterization of Neutral Silver(I) Complexes with Arenephosphinothiols. Crystal Structures of [Ag4{2-(Ph2P)-6-(Me3Si)C6H6S}4] and [Ag4{2-(Ph2PO)-6-(Me3Si)C6H3S}4] Inorg. Chem., 38, 538–544 (1999).

P.G. Jones, R. Terroba, E. Fernandez, M. Laguna, Tris(pentafluorophenyl)[2-(diphenylphosphino)thiophenol-P]gold(III) dichloromethane solvate, Acta Cryst. E, 58, m90–m92 (2002).

P. Perez-Lourido, J. Romero, J.A. Garcia-Vazquez, A. Sousa, K.P. Maresca, J. Zubieta, Synthesis and Characterization of Zinc and Cadmium Compounds with Arenephosphinothiol Ligands. Crystal and Molecular Structures of [Cd2{2-(Ph2PO)C6H4S}4], [Zn{2-(Ph2P)-6-(Me3Si)C6H3S}2], [Cd{2-(Ph2PO)-6-(Me3Si)C6H3S}2(CH3OH)], and [Zn{PhPO(C6H4S-2)2}(bipy)], Inorg. Chem., 38, 3709–3715 (1999).

P. Fernández, A. Sousa-Pedrares, J. Romero, J.A. García-Vázquez, A. Sousa, P. Pérez-Lourido, Zinc(II), Cadmium(II), Mercury(II), and Ethylmercury(II) Complexes of Phosphinothiol Ligands, Inorg. Chem., 47, 2121–2132 (2008).

P. Barbaro, F. Cecconi, C.A. Ghilardi, S. Midollini, A. Orlandini, A. Vacca, Metal Coordination and Hg-C Bond Protonolysis in Organomercury(II) Compounds. Synthesis, Characterization, and Reactivity of the Tetrahedral Complexes [(np3)HgR][(CF3)SO3] {np3 = N(CH2CH2PPh2)3; R = CH3, C2H5, C6H5}, Inorg. Chem., 33, 6163–6170 (1994).

A. Garoufis, S.P. Perlepes, A. Schreiber, R. Bau, N. Hadjiliadis, Mercury(II)-carbon bond cleavage due to the coordination of the metal by 2-(2′-pyridyl)quinoxaline (L): preparation and characterization of [Hg2I4L2] derived from the reaction of CH3HgI and L, Polyhedron, 15, 177–182 (1996).

J.S. Casas, M.S. García-Tasende, A. Sánchez, J. Sordo, E.M. Vázquez-López, Protodemetallation of pyridinephenylmercury(II) compounds by diphenyldithiophosphinic acid. The molecular and crystal structure of [Hg2(S2PPh2)4], Inorg. Chim. Acta, 256, 211–216 (1997).

M. Wilhelm, S. Deeken, E. Berssen, W. Saak, A. Lützen, R. Koch, H. Strasdeit, The First Structurally Authenticated Organomercury(1+) Thioether Complexes − Mercury−Carbon Bond Activation Related to the Mechanism of the Bacterial Enzyme Organomercurial Lyase, Eur. J. Inorg. Chem., 2004, 2301–2312 (2004).

P. Perez-Lourido, J. Romero, J.A. Garcia-Vazquez, A. Sousa, K. Maresca, J. Zubieta, Synthesis and Characterization of Indium Compounds with Phosphinothiol Ligands. The Crystal and Molecular Structures of [In{2-(Ph2P)C6H4S}3], [In{2-(Ph2P)-6-(Me3Si)C6H3S}2{2-(Ph2PO)-6-(Me3Si)C6H3S}], and [NMe4][In{PhP(C6H4S-2)2}2]∙CH3CN, Inorg. Chem., 38, 1293–1298 (1999).

P. Pérez-Lourido, J. Romero, J.A. Garcı́a-Vázquez, A. Sousa, J. Zubieta, U. Russo, Diorganotin(IV) derivatives of arenephosphinothiol ligands. The crystal structure of [Ph2Sn{2-(Ph2P)C6H4S}2] and [Me2Sn{2-(Ph2PO)-6-(Me3Si)C6H3S}2], J. Organomet. Chem., 595, 59–65 (2000).

E.J. Fernández, M.B. Hursthouse, M. Laguna, R. Terroba, Phosphinethiolate tin(IV)-11 group-metal derivatives. X-ray structure of [Au2Sn(tBu)2(C6F5)2(SC6H4PPh2)2], J. Organomet. Chem., 574, 207–212 (1999).

P. Pérez-Lourido, L. Valencia, J. Romero, J.A. García-Vázquez, A. Sousa, J. Zubieta, Bismuth(III) complexes derivatives of phosphinothiol ligands: The crystal structure of [Bi{2-(Ph2P)C6H4S}3], Polyhedron, 45, 200–203 (2012).

I. Sárosi, A. Hildebrand, P. Lönnecke, L. Silaghi-Dumitrescu, E. Hey-Hawkins, Reaction of a heterotopic P,SAs ligand with group 10 metal(II) complexes: As-S bond cleavage and the formation of two unusual trinuclear structural isomers for Pd and Pt, Dalton Trans., 41, 5326–5333 (2012).

I. Sárosi, M.B. Sárosi, E. Hey-Hawkins, L. Silaghi-Dumitrescu, Reaction of a heterotopic P,SAs ligand with group 10 metal(II) complexes: a theoretical study, Studia UBB Chemia, LVII, 139–146 (2012).




DOI: http://dx.doi.org/10.20450/mjcce.2013.285

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