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The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications pp 209–238Cite as

Pincer Complexes with Thione Sulfur Donors

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 54))

Abstract

Rapid development of pincer chemistry over the last several decades made a substantial contribution in extension of theoretical and practical organometallic chemistry as well as organic synthesis, catalysis, and materials science. This review is devoted to relatively new types of nonclassical pincer compounds bearing thione sulfur donors incorporated into thiophosphoryl and/or thioamide groups. The discussion is focused on synthetic aspects and structural features of symmetrical and hybrid S,C,S-pincer ligands and complexes with particular attention to the practically valuable properties.

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Notes

  1. 1.

    Due to peculiar structure and coordination chemistry, bis(diphenylphosphinosulfide)methane derivatives seem to represent a subject for separate discussion and are beyond the scope of the current review.

References

  1. Shaw BL, Moulton CJ (1976) J Chem Soc Dalton Trans 1020

    Google Scholar 

  2. Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750

    Article  CAS  Google Scholar 

  3. Singleton JT (2003) Tetrahedron 59:1837

    Article  CAS  Google Scholar 

  4. van der Boom ME, Milstein D (2003) Chem Rev 103:1759

    Article  Google Scholar 

  5. Morales-Morales D (2004) Rev Soc Quím Méx 48:338

    CAS  Google Scholar 

  6. Beletskaya IP, Cheprakov AV (2004) J Organomet Chem 689:4055

    Article  CAS  Google Scholar 

  7. Dupont J, Consorti CS, Spencer J (2005) Chem Rev 105:2527

    Article  CAS  Google Scholar 

  8. Moreno I, SanMartin R, Inés B, Herrero MT, Domínguez E (2009) Curr Org Chem 13:878

    Article  CAS  Google Scholar 

  9. Albrecht M (2010) Chem Rev 110:576

    Article  CAS  Google Scholar 

  10. Odinets IL, Aleksanyan DV, Kozlov VA (2010) Lett Org Chem 7:583

    Article  CAS  Google Scholar 

  11. Selander N, Szabó KJ (2011) Chem Rev 111:2048

    Article  CAS  Google Scholar 

  12. Niu J-L, Hao X-Q, Gong J-F, Song M-P (2011) Dalton Trans 40:5135

    Article  CAS  Google Scholar 

  13. Morales-Morales D, Jensen CM (eds) (2007) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  14. van Koten G, Milstein D (eds) (2013) Organometallic pincer chemistry. Topics in Organometallic Chemistry, vol 40. Springer, Heidelberg

    Google Scholar 

  15. Dunina VV, Gorunova ON (2004) Russ Chem Rev 73:309

    Article  CAS  Google Scholar 

  16. Dunina VV, Gorunova ON (2005) Russ Chem Rev 74:871

    Article  CAS  Google Scholar 

  17. Torres-Nieto J, Garcia JJ (2007) Desulfurization catalyzed by nickel PCP-pincer compounds 79. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  18. Morales-Morales D (2007) The chemistry of PCP pincer phosphinite transition metal complexes 151. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  19. Ozerov OV (2007) Rigid PNP pincer ligands and their transition metal complexes 287. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  20. Morales-Morales D (2008) Mini Rev Org Chem 5:141

    Article  CAS  Google Scholar 

  21. Leis W, Mayer HA, Kaska WC (2008) Coord Chem Rev 252:1787

    Article  CAS  Google Scholar 

  22. Serrano-Becerra JM, Morales-Morales D (2009) Curr Org Synth 6:169

    Article  CAS  Google Scholar 

  23. van der Vlugt JI, Reek JNH (2009) Angew Chem Int Ed 48:8832

    Article  Google Scholar 

  24. Poverenov E, Milstein D (2013) Noninnocent behavior of PCP and PCN ligands of late metal complexes 21. In: van Koten G, Milstein D (eds) Organometallic pincer chemistry. Topics in Organometallic Chemistry, vol 40. Springer, Heidelberg

    Google Scholar 

  25. Roddick DM (2013) Tuning of PCP pincer ligand electronic and steric properties 49. In: van Koten G, Milstein D (eds) Organometallic pincer chemistry. Topics in organometallic chemistry, vol 40. Springer, Heidelberg

    Google Scholar 

  26. Gelman D, Romm R (2013) PC(sp3)P transition metal pincer complexes: properties and catalytic applications 289. In: van Koten G, Milstein D (eds) Organometallic pincer chemistry. Topics in organometallic chemistry, vol 40. Springer, Heidelberg

    Google Scholar 

  27. Chase PA, van Koten G (2007) Nitrogen-based pincers: a versatile platform for organometallic chemistry 181. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  28. Ito J-I, Nishiyama H (2013) Optically active bis(oxazolinyl)phenyl metal complexes as multiponent catalysts 243. In: van Koten G, Milstein D (eds) Organometallic pincer chemistry. Topics in organometallic chemistry, vol 40. Springer, Heidelberg

    Google Scholar 

  29. Mézailles N, Le Floch P (2007) S-P-S and S-C-S pincer ligands in coordination chemistry and catalysis 235. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  30. Takahashi S, Nonoyama M, Kita M (1995) Trans Met Chem 20:528

    Article  CAS  Google Scholar 

  31. Scheibye S, Pedersen BS, Lawesson S-O (1978) Bull Soc Chim Belg 87:229

    Article  CAS  Google Scholar 

  32. Amupitan JO (1983) Synthesis 730

    Google Scholar 

  33. Nojima Y, Nonoyama M, Nakajima K (1996) Polyhedron 15:3795

    Article  CAS  Google Scholar 

  34. Akaiwa M, Kanbara T, Fukumoto H, Yamamoto T (2005) J Organomet Chem 690:4192

    Article  CAS  Google Scholar 

  35. Kuwabara J, Kanbara T (2008) J Photopolym Sci Technol 21:349

    Article  CAS  Google Scholar 

  36. Freeman GR, Williams JAG (2013) Metal complexes of pincer ligands: excited states, photochemistry, and luminescence 89. In: van Koten G, Milstein D (eds) Organometallic pincer chemistry. Topics in Organometallic Chemistry, vol. 40. Springer, Heidelberg

    Google Scholar 

  37. Ogawa Y, Taketoshi A, Kuwabara J, Okamoto K, Fukuda T, Kanbara T (2010) Chem Lett 39:385

    Article  CAS  Google Scholar 

  38. Kuwabara J, Ogawa Y, Taketoshi A, Kanbara T (2011) J Organomet Chem 696:1289

    Article  CAS  Google Scholar 

  39. Williams JAG, Develay S, Rochester DL, Murphy L (2008) Coord Chem Rev 252:2596

    Article  Google Scholar 

  40. Kanbara T, Okada K, Yamamoto T, Ogawa H, Inoue T (2004) J Organomet Chem 689:1860

    Article  CAS  Google Scholar 

  41. Okamoto K, Kanbara T, Yamamoto T, Wada A (2006) Organometallics 25:4026

    Article  CAS  Google Scholar 

  42. Okamoto K, Yamamoto T, Akita M, Wada A, Kanbara T (2009) Organometallics 28:3307

    Article  CAS  Google Scholar 

  43. Honda H, Ogawa Y, Kuwabara J, Kanbara T (2014) Eur J Inorg Chem 1865

    Google Scholar 

  44. Okamoto K, Kuwabara J, Kanbara T (2011) J Organomet Chem 696:1305

    Article  CAS  Google Scholar 

  45. Teratani T, Koizumi T-a, Yamamoto T, Kanbara T (2011) Inorg Chem Commun 14:836

    Google Scholar 

  46. Teratani T, Koizumi T, Yamamoto T, Tanaka K, Kanbara T (2011) Dalton Trans 40:8879

    Article  CAS  Google Scholar 

  47. Wang C-H, Ma N-N, Sun X-X, Sun S-L, Qiu Y-Q, Liu P-J (2012) J Phys Chem A 116:10496

    Article  CAS  Google Scholar 

  48. Koizumi T-a, Teratani T, Okamoto K, Yamamoto T, Shimoi Y, Kanbara T (2010) Inorg Chim Acta 363:2474

    Google Scholar 

  49. Okamoto K, Kanbara T, Yamamoto T (2006) Chem Lett 35:558

    Article  CAS  Google Scholar 

  50. Hossain MdA, Lucarini S, Powell D, Bowman-James K (2004) Inorg Chem 43:7275

    Google Scholar 

  51. Begum RA, Powell D, Bowman-James K (2006) Inorg Chem 45:964

    Article  CAS  Google Scholar 

  52. Wang H, Liu J, Deng Y, Min T, Yu G, Wu X, Yang Z, Lei A (2009) Chem Eur J 15:1499

    Article  CAS  Google Scholar 

  53. Liu J, Wang H, Zhang H, Wu X, Zhang H, Deng Y, Yang Z, Lei A (2009) Chem Eur J 15:4437

    Article  CAS  Google Scholar 

  54. Liu J, Deng Y, Lin C, Lei A (2012) Chem Sci 3:1211

    Article  CAS  Google Scholar 

  55. Wang Q-Q, Begum RA, Day VW, Bowman-James K (2012) Inorg Chem 51:760

    Article  Google Scholar 

  56. Komiyama Y, Kuwabara J, Kanbara T (2014) Organometallics 33:885

    Article  CAS  Google Scholar 

  57. Kuwabara J, Munezawa G, Okamoto K, Kanbara T (2010) Dalton Trans 39:6255

    Article  CAS  Google Scholar 

  58. Kanbara T, Yamamoto T (2003) J Organomet Chem 688:15

    Article  CAS  Google Scholar 

  59. Rybtchinski B, Milstein D (2007) Pincer systems as models for the activation of strong bonds: scope and mechanism 87. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  60. Montag M, Efremenko I, Diskin-Posner Y, Ben-David Y, Martin JML, Milstein D (2012) Organometallics 31:505

    Article  CAS  Google Scholar 

  61. Montag M, Efremenko I, Leitus G, Ben-David Y, Martin JML, Milstein D (2013) Organometallics 32:7163

    Article  CAS  Google Scholar 

  62. Meguro H, Koizumi T-A, Yamamoto T, Kanbara T (2008) J Organomet Chem 693:1109

    Article  CAS  Google Scholar 

  63. Heard PJ, Aliev AE (1998) Polyhedron 17:3981

    Article  CAS  Google Scholar 

  64. Leung W-P, Kan K-W, Mak TCW (2010) Organometallics 29:1890

    Article  CAS  Google Scholar 

  65. Fraix A, Lutz M, Spek AL, Klein Gebbink RJM, van Koten G, Salaün J-Y, Jaffrès P-A (2010) Dalton Trans 39:2942

    Article  CAS  Google Scholar 

  66. Stradiotto M, Kozak CM, McGlinchey MJ (1998) J Organomet Chem 564:101

    Article  CAS  Google Scholar 

  67. Oulié P, Nebra N, Saffon N, Maron L, Martin-Vaca B, Bourissou D (2009) J Am Chem Soc 131:3493

    Article  Google Scholar 

  68. Nebra N, Lisena J, Saffon N, Maron L, Martin-Vaca B, Bourissou D (2011) Dalton Trans 40:8912

    Article  CAS  Google Scholar 

  69. Nebra N, Saffon N, Maron L, Martin-Vaca B, Bourissou D (2011) Inorg Chem 50:6378

    Article  CAS  Google Scholar 

  70. Oulié P, Nebra N, Ladeira S, Martin-Vaca B, Bourissou D (2011) Organometallics 30:6416

    Article  Google Scholar 

  71. Lisena J, Monot J, Mallet-Ladeira S, Martin-Vaca B, Bourissou D (2013) Organometallics 32:4301

    Article  CAS  Google Scholar 

  72. Nicolas E, Martin-Vaca B, Mézailles N, Bourissou D, Maron L (2013) Eur J Inorg Chem 4068

    Google Scholar 

  73. Kozlov VA, Aleksanyan DV, Nelyubina YV, Lyssenko KA, Gutsul EI, Vasil’ev AA, Petrovskii PV, Odinets IL (2009) Dalton Trans 8657

    Google Scholar 

  74. Wang Z, Eberhard MR, Jensen CM, Matsukawa S, Yamamoto Y (2003) J Organomet Chem 681:189

    Article  CAS  Google Scholar 

  75. Gagliardo M, Selander N, Mehendale NC, van Koten G, Klein Gebbink RJM, Szabó KJ (2008) Chem Eur J 14:4800

    Article  CAS  Google Scholar 

  76. Zhang B-S, Wang C, Gong J-F, Song M-P (2009) J Organomet Chem 694:2555

    Article  CAS  Google Scholar 

  77. Hao X-Q, Wang Y-N, Liu J-R, Wang K-L, Gong J-F, Song M-P (2010) J Organomet Chem 695:82

    Article  CAS  Google Scholar 

  78. Jambor R, Dostál L (2007) Hypervalent organotin, aluminum, antimony and bismuth Y,C,Y-chelate complexes 357. In: Morales-Morales D, Jensen CM (eds) The chemistry of pincer compounds. Elsevier, Oxford

    Google Scholar 

  79. Fisher J, Schürman M, Mehring M, Zachwieja U, Jurkschat K (2006) Organometallics 25:2886

    Article  Google Scholar 

  80. Peveling K, Henn M, Löw C, Mehring M, Schürmann M, Costisella B, Jurkschat K (2004) Organometallics 23:1501

    Article  CAS  Google Scholar 

  81. Kozlov VA, Aleksanyan DV, Nelyubina YV, Lyssenko KA, Gutsul EI, Puntus LN, Vasil’ev AA, Petrovskii PV, Odinets IL (2008) Organometallics 27:4062

    Article  CAS  Google Scholar 

  82. Aleksanyan DV, Kozlov VA, Nelyubina YV, Lyssenko KA, Puntus LN, Gutsul EI, Shepel NE, Vasil’ev AA, Petrovskii PV, Odinets IL (2011) Dalton Trans 40:1535

    Article  CAS  Google Scholar 

  83. Zhang J, Leitus G, Ben-David Y, Milstein D (2006) Angew Chem Int Ed 45:1113

    Article  CAS  Google Scholar 

  84. Inés B, Moreno I, SanMartin R, Domínguez E (2008) J Org Chem 73:8448

    Article  Google Scholar 

  85. Yorke J, Sanford J, Decken A, Xia A (2010) Inorg Chim Acta 363:961

    Article  CAS  Google Scholar 

  86. Lindner R, van den Bosch B, Lutz M, Reek JNH, van der Vlugt JI (2011) Organometallics 30:499

    Article  CAS  Google Scholar 

  87. Aleksanyan DV, Kozlov VA, Shevchenko NE, Nenajdenko VG, Vasil’ev AA, Nelyubina YV, Ananyev IV, Petrovskii PV, Odinets IL (2012) J Organomet Chem 711:52

    Article  CAS  Google Scholar 

  88. Chakladar S, Paul P, Venkatsubramanian K, Nag K (1991) J Chem Soc Dalton Trans 2669

    Google Scholar 

  89. Chakladar S, Paul P, Nag K (1991) Polyhedron 10:1513

    Article  CAS  Google Scholar 

  90. Fernandez A, Pereira E, Fernandez JJ, Lopez-Torres M, Suarez A, Mosteiro R, Pereira MT, Vila JM (2002) New J Chem 26:895

    Article  CAS  Google Scholar 

  91. Kozlov VA, Aleksanyan DV, Nelyubina YV, Lyssenko KA, Vasil’ev AA, Petrovskii PV, Odinets IL (2010) Organometallics 29:2054

    Article  CAS  Google Scholar 

  92. Poverenov E, Efremenko I, Frenkel AI, Ben-David Y, Shimon LJW, Leitus G, Konstantinovski L, Martin JML, Milstein D (2008) Nature 455:1093

    Article  CAS  Google Scholar 

  93. Gai X, Grigg R, Collard S, Muir JE (2000) Chem Commun 1765

    Google Scholar 

  94. Grigg R, Khamnaen T, Rajviroongit S, Sridharan V (2002) Tetrahedron Lett 43:2601

    Article  CAS  Google Scholar 

  95. Gai X, Grigg R, Koppen I, Marchbank J, Sridharan V (2003) Tetrahedron Lett 44:7445

    Article  CAS  Google Scholar 

  96. Gai X, Grigg R, Ramzan MI, Sridharan V, Collard S, Muir JE (2000) Chem Commun 2053

    Google Scholar 

  97. Kozlov VA, Aleksanyan DV, Nelyubina YV, Lyssenko KA, Petrovskii PV, Vasil’ev AA, Odinets IL (2011) Organometallics 30:2920

    Article  CAS  Google Scholar 

  98. Kozlov VA, Aleksanyan DV, Korobov MV, Avramenko NV, Aysin RR, Maloshitskaya OA, Korlyukov AS, Odinets IL (2011) Dalton Trans 40:8768

    Article  CAS  Google Scholar 

  99. Aleksanyan DV, Klemenkova ZS, Vasil’ev AA, Gorenberg AY, Nelyubina YV, Kozlov VA (2015) Dalton Trans 44:3216

    Google Scholar 

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Acknowledgments

The authors are grateful to the Russian Foundation for Basic Research (project no. 14-03-31237-mol-a) and Council on Grants of the President of the Russian Federation (project no. MK-382.2014.3) for financial support.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    Diana V. Aleksanyan & Vladimir A. Kozlov

Authors
  1. Diana V. Aleksanyan
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  2. Vladimir A. Kozlov
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Correspondence to Diana V. Aleksanyan .

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Editors and Affiliations

  1. Organic Chemistry and Catalysis, Debye Institute for Nanomaterials Science, Utrecht University, Utrecht, The Netherlands

    Gerard van Koten

  2. Department of Chemistry & Biology, Ryerson University, Toronto, Canada

    Robert A Gossage

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Aleksanyan, D.V., Kozlov, V.A. (2015). Pincer Complexes with Thione Sulfur Donors. In: van Koten, G., Gossage, R. (eds) The Privileged Pincer-Metal Platform: Coordination Chemistry & Applications. Topics in Organometallic Chemistry, vol 54. Springer, Cham. https://doi.org/10.1007/3418_2015_115

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