Skip to main content
SpringerLink
Log in

PC(sp 3)P Transition Metal Pincer Complexes: Properties and Catalytic Applications

  • Chapter
  • First Online:
Organometallic Pincer Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 40))

Abstract

Carbometalated pincer complexes represent a family of powerful compounds having tremendous number of manifold applications in organometallic chemistry, synthesis, catalysis, material science, and bioinorganic chemistry. This chapter reviews the recent developments in the chemistry and catalytic applications of PC(sp 3)P transition metal pincer complexes stressing their singular reactivity that stem from the unique electronic properties and topology.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Shaw BL (1975) J Am Chem Soc 97:3856

    Article  CAS  Google Scholar 

  2. Dehand J, Pfeffer M (1976) Coord Chem Rev 18:327

    Article  CAS  Google Scholar 

  3. Newkome GR, Puckett WE, Gupta VK, Kiefer GE (1986) Chem Rev 86:451

    Article  CAS  Google Scholar 

  4. Moreno I, SanMartin R, Ines B, Churruca F, Dominguez E (2010) Inorg Chim Acta 363:1903

    Article  CAS  Google Scholar 

  5. van Koten G (1989) Pure Appl Chem 61:1681

    Article  Google Scholar 

  6. Benito-Garagorri D, Kirchner K (2008) Acc Chem Res 41:201

    Article  CAS  Google Scholar 

  7. Mayer HA, Kaska WC (1994) Chem Rev 94:1239

    Article  CAS  Google Scholar 

  8. Morales-Morales D (2008) Reactivity of pincer complexes toward carbon monooxide Wiley-VCH Verlag GmbH & Co. KGaA p 27

    Google Scholar 

  9. Limberg C (2009) Angew Chem Int Ed 48:2270

    Article  CAS  Google Scholar 

  10. Jensen CM (1999) Chem Commun 2443

    Google Scholar 

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

    Article  Google Scholar 

  12. Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761

    Article  CAS  Google Scholar 

  13. Gunanathan C, Milstein D (2011) Acc Chem Res 44:588

    Article  CAS  Google Scholar 

  14. Selander N, Szabo KJ (2011) Chem Rev 111:2048

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Slagt MQ, van Zwieten DAP, Moerkerk AJCM, Klein Gebbink RJM, van Koten G (2004) Coord Chem Rev 248:2275

    Article  CAS  Google Scholar 

  17. Lang H, Packheiser R, Walfort B (2006) Organometallics 25:1836

    Article  CAS  Google Scholar 

  18. Wieczorek B, Dijkstra HP, Egmond MR, Klein Gebbink RJM, van Koten G (2009) J Organomet Chem 694:812

    Article  CAS  Google Scholar 

  19. Guillena G, Kruithof CA, Casado MA, Egmond MR, van Koten G (2003) J Organomet Chem 668:3

    Article  CAS  Google Scholar 

  20. Stiriba S-E, Slagt MQ, Kautz H, Klein Gebbink RJM, Thomann R, Frey H, van Koten G (2004) Chem Eur J 10:1267

    Article  CAS  Google Scholar 

  21. Gerhardt WW, Zucchero AJ, Wilson JN, South CR, Bunz UHF, Weck M (2006) Chem Commun 20:2141

    Article  Google Scholar 

  22. Chen Y, Li K, Lu W, Chui SS-Y, Ma C-W, Che C-M (2009) Angew Chem Int Ed 48:9909

    Article  CAS  Google Scholar 

  23. Suijkerbuijk BMJM, Schamhart DJ, Kooijman H, Spek AL, van Koten G, Klein Gebbink RJM (2010) Dalton Trans 39:6198

    Article  CAS  Google Scholar 

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

    Google Scholar 

  25. Creaser CS, Kaska WC (1978) Inorg Chim Acta 30:L325

    Article  CAS  Google Scholar 

  26. van Koten G, Timmer K, Noltes JG, Spek AL (1978) J Chem Soc Chem Commun 250

    Google Scholar 

  27. van de Kuil LA, Luitjes H, Grove DM, Zwikker JW, van der Linden JGM, Roelofsen AM, Jenneskens LW, Drenth W, van Koten G (1994) Organometallics 13:468

    Article  Google Scholar 

  28. Mohammad HAY, Grimm JC, Eichele K, Mack H-G, Speiser B, Novak F, Quintanilla MG, Kaska WC, Mayer HA (2002) Organometallics 21:5775

    Article  CAS  Google Scholar 

  29. Riehl JF, Jean Y, Eisenstein O, Pelissier M (1992) Organometallics 11:729

    Article  CAS  Google Scholar 

  30. Crocker C, Empsall HD, Errington RJ, Hyde EM, McDonald WS, Markham R, Norton MC, Shaw BL, Weeks B (1982) J Chem Soc Dalton Trans 1217

    Google Scholar 

  31. Errington RJ, McDonald WS, Shaw BL (1982) J Chem Soc Dalton Trans 1829

    Google Scholar 

  32. Vigalok A, Milstein D (2000) Organometallics 19:2061

    Article  CAS  Google Scholar 

  33. Tulloch AAD, Danopoulos AA, Tizzard GJ, Coles SJ, Hursthouse MB, Hay-Motherwell RS, Motherwell WB (2001) Chem Commun 1270

    Google Scholar 

  34. Nielsen DJ, Cavell KJ, Skelton BW, White AH (2002) Inorg Chim Acta 327:116

    Article  CAS  Google Scholar 

  35. Danopoulos AA, Tulloch AAD, Winston S, Eastham G, Hursthouse MB (2003) Dalton Trans 1009

    Google Scholar 

  36. Diez-Barra E, Guerra J, Lopez-Solera I, Merino S, Rodriguez-Lopez J, Sanchez-Verdu P, Tejeda J (2003) Organometallics 22:541

    Article  CAS  Google Scholar 

  37. Lee HM, Zeng JY, Hu C-H, Lee M-T (2004) Inorg Chem 43:6822

    Article  CAS  Google Scholar 

  38. Nilsson P, Wendt OF (2005) J Organomet Chem 690:4197

    Article  CAS  Google Scholar 

  39. Ma L, Woloszynek RA, Chen W, Ren T, Protasiewicz JD (2006) Organometallics 25:3301

    Article  CAS  Google Scholar 

  40. Olsson D, Arunachalampillai A, Wendt OF (2007) Dalton Trans 5427

    Google Scholar 

  41. Morgan BP, Galdamez GA, Gilliard RJ Jr, Smith RC (2009) Dalton Trans 2020

    Google Scholar 

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

    Article  CAS  Google Scholar 

  43. Mayer HA, Fawzi R, Steimann M (1993) Chem Ber 126:1341

    Article  CAS  Google Scholar 

  44. Gerber R, Fox T, Frech C (2010) Chem Eur J 16:6771

    Article  CAS  Google Scholar 

  45. Nemeh S, Flesher RJ, Gierling K, Maichle-Moessmer C, Mayer HA, Kaska WC (1998) Organometallics 17:2003

    Article  CAS  Google Scholar 

  46. Gozin M, Weisman A, Ben-David Y, Milstein D (1993) Nature 364:699

    Article  CAS  Google Scholar 

  47. Weng W, Parkin S, Ozerov OV (2006) Organometallics 25:5345

    Article  CAS  Google Scholar 

  48. Hoskins SV, Rickard CEF, Roper WR (1984) J. Chem Soc, Chem Commun 1000

    Google Scholar 

  49. Ciclosi M, Lloret J, Estevan F, Lahuerta P, Sanau M, Perez-Prieto J (2006) Angew Chem Int Ed 45:6741

    Article  CAS  Google Scholar 

  50. Koridze AA, Polezhaev AV, Safronov SV, Sheloumov AM, Dolgushin FM, Ezernitskaya MG, Lokshin BV, Petrovskii PV, Peregudov AS (2010) Organometallics 29:4360

    Article  CAS  Google Scholar 

  51. Azerraf C, Gelman D (2008) Chem Eur J 14:10364

    Article  CAS  Google Scholar 

  52. Empsall HD, Hyde EM, Markham R, McDonald WS, Norton MC, Shaw BL, Weeks B (1977) J Chem Soc Chem Commun 589

    Google Scholar 

  53. Crocker C, Errington RJ, McDonald WS, Odell KJ, Shaw BL, Goodfellow RJ (1979) J Chem Soc Chem Commun 498

    Google Scholar 

  54. Gusev DG, Lough AJ (2002) Organometallics 21:2601

    Article  CAS  Google Scholar 

  55. Gusev DG, Lough AJ (2002) Organometallics 21:5091

    Article  CAS  Google Scholar 

  56. Al-Salem NA, Empsall HD, Markham R, Shaw BL, Weeks B (1979) J Chem Soc Dalton Trans 1972

    Google Scholar 

  57. Castonguay A, Sui-Seng C, Zargarian D, Beauchamp AL (2006) Organometallics 25:602

    Article  CAS  Google Scholar 

  58. Zhao J, Goldman AS, Hartwig JF (2005) Science 307:1080

    Article  CAS  Google Scholar 

  59. Bursten BE, Chen S, Chisholm MH (2008) J Organomet Chem 693:1547

    Article  CAS  Google Scholar 

  60. Huang Z, Zhou J, Hartwig JF (2010) J Am Chem Soc 132:11458

    Article  CAS  Google Scholar 

  61. Vigalok A, Ben-David Y, Milstein D (1996) Organometallics 15:1839

    Article  CAS  Google Scholar 

  62. McLoughlin MA, Keder NL, Harrison WTA, Flesher RJ, Mayer HA, Kaska WC (1999) Inorg Chem 38:3223

    Article  CAS  Google Scholar 

  63. Huang K-W, Han JH, Musgrave CB, Fujita E (2007) Organometallics 26:508

    Article  CAS  Google Scholar 

  64. Vigalok A, Kraatz H-B, Konstantinovsky L, Milstein D (1997) Chem Eur J 3:253

    Article  CAS  Google Scholar 

  65. Zhou J, Hartwig JF (2008) Angew Chem Int Ed 47:5783

    Article  CAS  Google Scholar 

  66. Pandarus V, Zargarian D (2007) Chem Commun 978

    Google Scholar 

  67. Pandarus V, Zargarian D (2007) Organometallics 26:4321

    Article  CAS  Google Scholar 

  68. Castonguay A, Beauchamp AL, Zargarian D (2008) Organometallics 27:5723

    Article  CAS  Google Scholar 

  69. Castonguay A, Spasyuk DM, Madern N, Beauchamp AL, Zargarian D (2009) Organometallics 28:2134

    Article  CAS  Google Scholar 

  70. Mayer HA, Kaska WC (1990) Chem Ber 123:1827

    Article  CAS  Google Scholar 

  71. Sjoevall S, Wendt OF, Andersson C (2002) J Chem Soc Dalton Trans 1396

    Google Scholar 

  72. Kuznetsov VF, Lough AJ, Gusev DG (2006) Inorg Chim Acta 359:2806

    Article  CAS  Google Scholar 

  73. Olsson D, Janse VRJM, Wendt OF (2007) Acta Crystallogr Sect E Struct Rep Online E63:m1969

    Article  Google Scholar 

  74. Arunachalampillai A, Olsson D, Wendt OF (2009) Dalton Trans 8626

    Google Scholar 

  75. Olsson D, Wendt OF (2009) J Organomet Chem 694:3112

    Article  CAS  Google Scholar 

  76. Gerber R, Blacque O, Frech C (2009) ChemCatChem 1:393

    Article  CAS  Google Scholar 

  77. Gerber R, Blacque O, Frech CM (2011) Dalton Trans 40(35):8996

    Article  CAS  Google Scholar 

  78. Djakovitch L, Koehler K, de VJG (2008) The role of palladium nanoparticles as catalysts for carbon-carbon reactions. Wiley-VCH Verlag GmbH & Co. KGaA p 303

    Google Scholar 

  79. Winter AM, Eichele K, Mack H-G, Kaska WC, Mayer HA (2005) Organometallics 24:1837

    Article  CAS  Google Scholar 

  80. Winter AM, Eichele K, Mack H-G, Kaska WC, Mayer HA (2008) Dalton Trans 527

    Google Scholar 

  81. Rybtchinski B, Vigalok A, Ben-David Y, Milstein D (1996) J Am Chem Soc 118:12406

    Article  CAS  Google Scholar 

  82. van der Boom ME, Kraatz H-B, Hassner L, Ben-David Y, Milstein D (1999) Organometallics 18:3873

    Article  Google Scholar 

  83. van der Boom ME, Liou S-Y, Shimon LJW, Ben-David Y, Milstein D (2004) Inorg Chim Acta 357:4015

    Article  Google Scholar 

  84. Ohff M, Ohff A, van der Boom ME, Milstein D (1997) J Am Chem Soc 119:11687

    Article  CAS  Google Scholar 

  85. Gozin M, Alzenberg M, Liou S-Y, Weisman A, Ben-David Y, Milstein D (1994) Nature 370:42

    Article  CAS  Google Scholar 

  86. Cohen R, van der Boom ME, Shimon LJW, Rozenberg H, Milstein D (2000) J Am Chem Soc 122:7723

    Article  CAS  Google Scholar 

  87. Sundermann A, Uzan O, Milstein D, Martin JML (2000) J Am Chem Soc 122:7095

    Article  CAS  Google Scholar 

  88. Cohen R, Milstein D, Martin JML (2004) Organometallics 23:2336

    Article  CAS  Google Scholar 

  89. Cao Z, Hall MB (2000) Organometallics 19:3338

    Article  CAS  Google Scholar 

  90. Lesueur W, Solari E, Floriani C, Chiesi-Villa A, Rizzoli C (1997) Inorg Chem 36:3354

    Article  CAS  Google Scholar 

  91. Ciclosi M, Estevan F, Lahuerta P, Passarelli V, Perez-Prieto J, Sanau M (2008) Adv Synth Catal 350:234

    Article  CAS  Google Scholar 

  92. Ciclosi M, Estevan F, Lahuerta P, Passarelli V, Perez-Prieto J, Sanau M (2009) Dalton Trans 2290

    Google Scholar 

  93. Schwartz LH (1968) J Org Chem 33:3977

    Article  CAS  Google Scholar 

  94. Grossman O, Azerraf C, Gelman D (2006) Organometallics 25:375

    Article  CAS  Google Scholar 

  95. Ahlers W, Roeper M, Hofmann P, Warth DCM, Paciello R (2001) BASF A.-G., Germany p 51

    Google Scholar 

  96. Schnetz T, Roeder M, Rominger F, Hofmann P (2008) Dalton Trans 2238

    Google Scholar 

  97. Azerraf C, Gelman D (2009) Organometallics 28:6578

    Article  CAS  Google Scholar 

  98. Azerraf C (2010) PhD thesis, The Hebrew University

    Google Scholar 

  99. Musa S, Romm R, Azerraf C, Kozuch S, Gelman D (2011) Dalton Trans 40(35):8760

    Article  CAS  Google Scholar 

  100. Azerraf C, Shpruhman A, Gelman D (2009) Chem Commun 466

    Google Scholar 

  101. Haenel MW, Jakubik D, Krueger C, Betz P (1991) Chem Ber 124:333

    Article  CAS  Google Scholar 

  102. Levy R, Azerraf C, Gelman D, Rueck-Braun K, Kapoor PN (2009) Catal Commun 11:298

    Article  CAS  Google Scholar 

  103. Musa S, Shaposhnikov I, Cohen S, Gelman D (2011) Angew Chem Int Ed 50:3533

    Article  CAS  Google Scholar 

  104. Zhang J, Leitus G, Ben-David Y, Milstein D (2005) J Am Chem Soc 127:10840

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry, The Hebrew University, Edmund Safra Campus, 91904, Jerusalem, Israel

    Dmitri Gelman & Ronit Romm

Authors
  1. Dmitri Gelman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ronit Romm
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Dmitri Gelman .

Editor information

Editors and Affiliations

  1. Debye Research Institute, Department of Metal-Mediated Synthesis, Utrecht University, Padualaan 8, Utrecht, 3584, Netherlands

    Gerard van Koten

  2. The Kimmel Center for Molecular Design, Department of Organic Chemistry, The Weizmann Institute of Science, no street, Rehovot, 76100, Israel

    David Milstein

Rights and permissions

Reprints and permissions

Copyright information

© 2013 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Gelman, D., Romm, R. (2013). PC(sp 3)P Transition Metal Pincer Complexes: Properties and Catalytic Applications. In: van Koten, G., Milstein, D. (eds) Organometallic Pincer Chemistry. Topics in Organometallic Chemistry, vol 40. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-31081-2_10

Download citation

Publish with us

Policies and ethics

Search

Navigation