Advertisement

PC(sp3)P Transition Metal Pincer Complexes: Properties and Catalytic Applications

  • Dmitri GelmanEmail author
  • Ronit Romm
Chapter
First Online:
Part of the Topics in Organometallic Chemistry book series (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.

Keywords

catalysis pincer sp3-carbometalated 
This is a preview of subscription content, log in to check access.

References

  1. 1.
    Shaw BL (1975) J Am Chem Soc 97:3856CrossRefGoogle Scholar
  2. 2.
    Dehand J, Pfeffer M (1976) Coord Chem Rev 18:327CrossRefGoogle Scholar
  3. 3.
    Newkome GR, Puckett WE, Gupta VK, Kiefer GE (1986) Chem Rev 86:451CrossRefGoogle Scholar
  4. 4.
    Moreno I, SanMartin R, Ines B, Churruca F, Dominguez E (2010) Inorg Chim Acta 363:1903CrossRefGoogle Scholar
  5. 5.
    van Koten G (1989) Pure Appl Chem 61:1681CrossRefGoogle Scholar
  6. 6.
    Benito-Garagorri D, Kirchner K (2008) Acc Chem Res 41:201CrossRefGoogle Scholar
  7. 7.
    Mayer HA, Kaska WC (1994) Chem Rev 94:1239CrossRefGoogle Scholar
  8. 8.
    Morales-Morales D (2008) Reactivity of pincer complexes toward carbon monooxide Wiley-VCH Verlag GmbH & Co. KGaA p 27Google Scholar
  9. 9.
    Limberg C (2009) Angew Chem Int Ed 48:2270CrossRefGoogle Scholar
  10. 10.
    Jensen CM (1999) Chem Commun 2443Google Scholar
  11. 11.
    van der Boom ME, Milstein D (2003) Chem Rev 103:1759CrossRefGoogle Scholar
  12. 12.
    Choi J, MacArthur AHR, Brookhart M, Goldman AS (2011) Chem Rev 111:1761CrossRefGoogle Scholar
  13. 13.
    Gunanathan C, Milstein D (2011) Acc Chem Res 44:588CrossRefGoogle Scholar
  14. 14.
    Selander N, Szabo KJ (2011) Chem Rev 111:2048CrossRefGoogle Scholar
  15. 15.
    Albrecht M, van Koten G (2001) Angew Chem Int Ed 40:3750CrossRefGoogle Scholar
  16. 16.
    Slagt MQ, van Zwieten DAP, Moerkerk AJCM, Klein Gebbink RJM, van Koten G (2004) Coord Chem Rev 248:2275CrossRefGoogle Scholar
  17. 17.
    Lang H, Packheiser R, Walfort B (2006) Organometallics 25:1836CrossRefGoogle Scholar
  18. 18.
    Wieczorek B, Dijkstra HP, Egmond MR, Klein Gebbink RJM, van Koten G (2009) J Organomet Chem 694:812CrossRefGoogle Scholar
  19. 19.
    Guillena G, Kruithof CA, Casado MA, Egmond MR, van Koten G (2003) J Organomet Chem 668:3CrossRefGoogle Scholar
  20. 20.
    Stiriba S-E, Slagt MQ, Kautz H, Klein Gebbink RJM, Thomann R, Frey H, van Koten G (2004) Chem Eur J 10:1267CrossRefGoogle Scholar
  21. 21.
    Gerhardt WW, Zucchero AJ, Wilson JN, South CR, Bunz UHF, Weck M (2006) Chem Commun 20:2141CrossRefGoogle Scholar
  22. 22.
    Chen Y, Li K, Lu W, Chui SS-Y, Ma C-W, Che C-M (2009) Angew Chem Int Ed 48:9909CrossRefGoogle Scholar
  23. 23.
    Suijkerbuijk BMJM, Schamhart DJ, Kooijman H, Spek AL, van Koten G, Klein Gebbink RJM (2010) Dalton Trans 39:6198CrossRefGoogle Scholar
  24. 24.
    Moulton CJ, Shaw BL (1976) J Chem Soc Dalton Trans 1020Google Scholar
  25. 25.
    Creaser CS, Kaska WC (1978) Inorg Chim Acta 30:L325CrossRefGoogle Scholar
  26. 26.
    van Koten G, Timmer K, Noltes JG, Spek AL (1978) J Chem Soc Chem Commun 250Google Scholar
  27. 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 13:468CrossRefGoogle Scholar
  28. 28.
    Mohammad HAY, Grimm JC, Eichele K, Mack H-G, Speiser B, Novak F, Quintanilla MG, Kaska WC, Mayer HA (2002) Organometallics 21:5775CrossRefGoogle Scholar
  29. 29.
    Riehl JF, Jean Y, Eisenstein O, Pelissier M (1992) Organometallics 11:729CrossRefGoogle Scholar
  30. 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 1217Google Scholar
  31. 31.
    Errington RJ, McDonald WS, Shaw BL (1982) J Chem Soc Dalton Trans 1829Google Scholar
  32. 32.
    Vigalok A, Milstein D (2000) Organometallics 19:2061CrossRefGoogle Scholar
  33. 33.
    Tulloch AAD, Danopoulos AA, Tizzard GJ, Coles SJ, Hursthouse MB, Hay-Motherwell RS, Motherwell WB (2001) Chem Commun 1270Google Scholar
  34. 34.
    Nielsen DJ, Cavell KJ, Skelton BW, White AH (2002) Inorg Chim Acta 327:116CrossRefGoogle Scholar
  35. 35.
    Danopoulos AA, Tulloch AAD, Winston S, Eastham G, Hursthouse MB (2003) Dalton Trans 1009Google Scholar
  36. 36.
    Diez-Barra E, Guerra J, Lopez-Solera I, Merino S, Rodriguez-Lopez J, Sanchez-Verdu P, Tejeda J (2003) Organometallics 22:541CrossRefGoogle Scholar
  37. 37.
    Lee HM, Zeng JY, Hu C-H, Lee M-T (2004) Inorg Chem 43:6822CrossRefGoogle Scholar
  38. 38.
    Nilsson P, Wendt OF (2005) J Organomet Chem 690:4197CrossRefGoogle Scholar
  39. 39.
    Ma L, Woloszynek RA, Chen W, Ren T, Protasiewicz JD (2006) Organometallics 25:3301CrossRefGoogle Scholar
  40. 40.
    Olsson D, Arunachalampillai A, Wendt OF (2007) Dalton Trans 5427Google Scholar
  41. 41.
    Morgan BP, Galdamez GA, Gilliard RJ Jr, Smith RC (2009) Dalton Trans 2020Google Scholar
  42. 42.
    Niu J-L, Hao X-Q, Gong J-F, Song M-P (2011) Dalton Trans 40:5135CrossRefGoogle Scholar
  43. 43.
    Mayer HA, Fawzi R, Steimann M (1993) Chem Ber 126:1341CrossRefGoogle Scholar
  44. 44.
    Gerber R, Fox T, Frech C (2010) Chem Eur J 16:6771CrossRefGoogle Scholar
  45. 45.
    Nemeh S, Flesher RJ, Gierling K, Maichle-Moessmer C, Mayer HA, Kaska WC (1998) Organometallics 17:2003CrossRefGoogle Scholar
  46. 46.
    Gozin M, Weisman A, Ben-David Y, Milstein D (1993) Nature 364:699CrossRefGoogle Scholar
  47. 47.
    Weng W, Parkin S, Ozerov OV (2006) Organometallics 25:5345CrossRefGoogle Scholar
  48. 48.
    Hoskins SV, Rickard CEF, Roper WR (1984) J. Chem Soc, Chem Commun 1000Google Scholar
  49. 49.
    Ciclosi M, Lloret J, Estevan F, Lahuerta P, Sanau M, Perez-Prieto J (2006) Angew Chem Int Ed 45:6741CrossRefGoogle Scholar
  50. 50.
    Koridze AA, Polezhaev AV, Safronov SV, Sheloumov AM, Dolgushin FM, Ezernitskaya MG, Lokshin BV, Petrovskii PV, Peregudov AS (2010) Organometallics 29:4360CrossRefGoogle Scholar
  51. 51.
    Azerraf C, Gelman D (2008) Chem Eur J 14:10364CrossRefGoogle Scholar
  52. 52.
    Empsall HD, Hyde EM, Markham R, McDonald WS, Norton MC, Shaw BL, Weeks B (1977) J Chem Soc Chem Commun 589Google Scholar
  53. 53.
    Crocker C, Errington RJ, McDonald WS, Odell KJ, Shaw BL, Goodfellow RJ (1979) J Chem Soc Chem Commun 498Google Scholar
  54. 54.
    Gusev DG, Lough AJ (2002) Organometallics 21:2601CrossRefGoogle Scholar
  55. 55.
    Gusev DG, Lough AJ (2002) Organometallics 21:5091CrossRefGoogle Scholar
  56. 56.
    Al-Salem NA, Empsall HD, Markham R, Shaw BL, Weeks B (1979) J Chem Soc Dalton Trans 1972Google Scholar
  57. 57.
    Castonguay A, Sui-Seng C, Zargarian D, Beauchamp AL (2006) Organometallics 25:602CrossRefGoogle Scholar
  58. 58.
    Zhao J, Goldman AS, Hartwig JF (2005) Science 307:1080CrossRefGoogle Scholar
  59. 59.
    Bursten BE, Chen S, Chisholm MH (2008) J Organomet Chem 693:1547CrossRefGoogle Scholar
  60. 60.
    Huang Z, Zhou J, Hartwig JF (2010) J Am Chem Soc 132:11458CrossRefGoogle Scholar
  61. 61.
    Vigalok A, Ben-David Y, Milstein D (1996) Organometallics 15:1839CrossRefGoogle Scholar
  62. 62.
    McLoughlin MA, Keder NL, Harrison WTA, Flesher RJ, Mayer HA, Kaska WC (1999) Inorg Chem 38:3223CrossRefGoogle Scholar
  63. 63.
    Huang K-W, Han JH, Musgrave CB, Fujita E (2007) Organometallics 26:508CrossRefGoogle Scholar
  64. 64.
    Vigalok A, Kraatz H-B, Konstantinovsky L, Milstein D (1997) Chem Eur J 3:253CrossRefGoogle Scholar
  65. 65.
    Zhou J, Hartwig JF (2008) Angew Chem Int Ed 47:5783CrossRefGoogle Scholar
  66. 66.
    Pandarus V, Zargarian D (2007) Chem Commun 978Google Scholar
  67. 67.
    Pandarus V, Zargarian D (2007) Organometallics 26:4321CrossRefGoogle Scholar
  68. 68.
    Castonguay A, Beauchamp AL, Zargarian D (2008) Organometallics 27:5723CrossRefGoogle Scholar
  69. 69.
    Castonguay A, Spasyuk DM, Madern N, Beauchamp AL, Zargarian D (2009) Organometallics 28:2134CrossRefGoogle Scholar
  70. 70.
    Mayer HA, Kaska WC (1990) Chem Ber 123:1827CrossRefGoogle Scholar
  71. 71.
    Sjoevall S, Wendt OF, Andersson C (2002) J Chem Soc Dalton Trans 1396Google Scholar
  72. 72.
    Kuznetsov VF, Lough AJ, Gusev DG (2006) Inorg Chim Acta 359:2806CrossRefGoogle Scholar
  73. 73.
    Olsson D, Janse VRJM, Wendt OF (2007) Acta Crystallogr Sect E Struct Rep Online E63:m1969CrossRefGoogle Scholar
  74. 74.
    Arunachalampillai A, Olsson D, Wendt OF (2009) Dalton Trans 8626Google Scholar
  75. 75.
    Olsson D, Wendt OF (2009) J Organomet Chem 694:3112CrossRefGoogle Scholar
  76. 76.
    Gerber R, Blacque O, Frech C (2009) ChemCatChem 1:393CrossRefGoogle Scholar
  77. 77.
    Gerber R, Blacque O, Frech CM (2011) Dalton Trans 40(35):8996CrossRefGoogle Scholar
  78. 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 303Google Scholar
  79. 79.
    Winter AM, Eichele K, Mack H-G, Kaska WC, Mayer HA (2005) Organometallics 24:1837CrossRefGoogle Scholar
  80. 80.
    Winter AM, Eichele K, Mack H-G, Kaska WC, Mayer HA (2008) Dalton Trans 527Google Scholar
  81. 81.
    Rybtchinski B, Vigalok A, Ben-David Y, Milstein D (1996) J Am Chem Soc 118:12406CrossRefGoogle Scholar
  82. 82.
    van der Boom ME, Kraatz H-B, Hassner L, Ben-David Y, Milstein D (1999) Organometallics 18:3873CrossRefGoogle Scholar
  83. 83.
    van der Boom ME, Liou S-Y, Shimon LJW, Ben-David Y, Milstein D (2004) Inorg Chim Acta 357:4015CrossRefGoogle Scholar
  84. 84.
    Ohff M, Ohff A, van der Boom ME, Milstein D (1997) J Am Chem Soc 119:11687CrossRefGoogle Scholar
  85. 85.
    Gozin M, Alzenberg M, Liou S-Y, Weisman A, Ben-David Y, Milstein D (1994) Nature 370:42CrossRefGoogle Scholar
  86. 86.
    Cohen R, van der Boom ME, Shimon LJW, Rozenberg H, Milstein D (2000) J Am Chem Soc 122:7723CrossRefGoogle Scholar
  87. 87.
    Sundermann A, Uzan O, Milstein D, Martin JML (2000) J Am Chem Soc 122:7095CrossRefGoogle Scholar
  88. 88.
    Cohen R, Milstein D, Martin JML (2004) Organometallics 23:2336CrossRefGoogle Scholar
  89. 89.
    Cao Z, Hall MB (2000) Organometallics 19:3338CrossRefGoogle Scholar
  90. 90.
    Lesueur W, Solari E, Floriani C, Chiesi-Villa A, Rizzoli C (1997) Inorg Chem 36:3354CrossRefGoogle Scholar
  91. 91.
    Ciclosi M, Estevan F, Lahuerta P, Passarelli V, Perez-Prieto J, Sanau M (2008) Adv Synth Catal 350:234CrossRefGoogle Scholar
  92. 92.
    Ciclosi M, Estevan F, Lahuerta P, Passarelli V, Perez-Prieto J, Sanau M (2009) Dalton Trans 2290Google Scholar
  93. 93.
    Schwartz LH (1968) J Org Chem 33:3977CrossRefGoogle Scholar
  94. 94.
    Grossman O, Azerraf C, Gelman D (2006) Organometallics 25:375CrossRefGoogle Scholar
  95. 95.
    Ahlers W, Roeper M, Hofmann P, Warth DCM, Paciello R (2001) BASF A.-G., Germany p 51Google Scholar
  96. 96.
    Schnetz T, Roeder M, Rominger F, Hofmann P (2008) Dalton Trans 2238Google Scholar
  97. 97.
    Azerraf C, Gelman D (2009) Organometallics 28:6578CrossRefGoogle Scholar
  98. 98.
    Azerraf C (2010) PhD thesis, The Hebrew UniversityGoogle Scholar
  99. 99.
    Musa S, Romm R, Azerraf C, Kozuch S, Gelman D (2011) Dalton Trans 40(35):8760CrossRefGoogle Scholar
  100. 100.
    Azerraf C, Shpruhman A, Gelman D (2009) Chem Commun 466Google Scholar
  101. 101.
    Haenel MW, Jakubik D, Krueger C, Betz P (1991) Chem Ber 124:333CrossRefGoogle Scholar
  102. 102.
    Levy R, Azerraf C, Gelman D, Rueck-Braun K, Kapoor PN (2009) Catal Commun 11:298CrossRefGoogle Scholar
  103. 103.
    Musa S, Shaposhnikov I, Cohen S, Gelman D (2011) Angew Chem Int Ed 50:3533CrossRefGoogle Scholar
  104. 104.
    Zhang J, Leitus G, Ben-David Y, Milstein D (2005) J Am Chem Soc 127:10840CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  1. 1.Institute of ChemistryThe Hebrew UniversityJerusalemIsrael

Personalised recommendations

Cite chapter

Buy options