Palladium(III) in Synthesis and Catalysis

Abstract

While the organometallic chemistry of Pd in its (0), (+II), and (+IV) oxidation states is well established, organometallic Pd(III) chemistry remains widely unexplored. Few characterized Pd(III) complexes are known, which has inhibited detailed study of the organometallic chemistry of Pd(III). In this review, the potential roles of both mono- and dinuclear Pd(III) complexes in organometallic chemistry are discussed. While not widely recognized, Pd in the (+III) oxidation state may play a significant role in a variety of known Pd-catalyzed reactions.

Graphical Abstract

Keywords

Bimetallic redox chemistry C–H functionalization Metal–metal bonding Pd(III) 

References

  1. 1.
    Negishi E (ed) (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley, New YorkGoogle Scholar
  2. 2.
    Murahashi T, Kurosawa H (2002) Coord Chem Rev 231:207–228CrossRefGoogle Scholar
  3. 3.
    Markert C, Neuburger M, Kulicke K, Meuwly M, Pfaltz A (2007) Angew Chem Int Ed 46:5892–5895CrossRefGoogle Scholar
  4. 4.
    Hama T, Hartwig JF (2008) Org Lett 10:1545–1548CrossRefGoogle Scholar
  5. 5.
    Albright TA (1982) Tetrahedron 38:1339–1388CrossRefGoogle Scholar
  6. 6.
    Miessler GL, Tarr DA (2004) Inorganic chemistry. Pearson Education, Upper Saddle River, New JerseyGoogle Scholar
  7. 7.
    Canty AJ, Gardiner MG, Jones RC, Rodemann T, Sharma M (2009) J Am Chem Soc 131:7236–7237CrossRefGoogle Scholar
  8. 8.
    Bonnington KJ, Jennings MC, Puddephatt RJ (2008) Organometallics 27:6521–6530CrossRefGoogle Scholar
  9. 9.
    Roundhill DM, Gray HB, Che CM (1989) Acc Chem Res 22:55–61CrossRefGoogle Scholar
  10. 10.
    Matsumoto K, Sakai K (2000) Adv Inorg Chem 49:375–427CrossRefGoogle Scholar
  11. 11.
    Lippert B (1999) Coord Chem Rev 182:263–295CrossRefGoogle Scholar
  12. 12.
    Zipp AP (1988) Coord Chem Rev 84:47–83CrossRefGoogle Scholar
  13. 13.
    Blake AJ, Gould RO, Holder AJ, Hyde TI, Lavery AJ, Odulate MO, Schröder M (1987) J Chem Soc Chem Commun 118–120Google Scholar
  14. 14.
    Usón R, Forniés J, Tomás M, Menjón B, Sünkel K, Bau R (1984) J Chem Soc Chem Commun 751–752Google Scholar
  15. 15.
    Usón R, Forniés J, Tomás M, Menjón B, Bau R, Sünkel K, Kuwabara E (1986) Organometallics 5:1576–1581CrossRefGoogle Scholar
  16. 16.
    Nyholm RS, Sharpe AG (1952) J Chem Soc 3579–3587Google Scholar
  17. 17.
    Sharpe AG (1950) J Chem Soc 3444–3450Google Scholar
  18. 18.
    Bartlett N, Rao PR (1964) Proc Chem Soc Lond 393–394Google Scholar
  19. 19.
    Tressaud A, Wintenberger M, Bartlett N, Hagenmuller P (1976) C R Acad Sci Paris 282:1069–1072Google Scholar
  20. 20.
    Tressaud A, Khairoun S, Dance JM, Grannec J, Portier J, Hagenmuller P (1982) J Fluorine Chem 21:28CrossRefGoogle Scholar
  21. 21.
    Tressaud A, Khairoun S, Dance JM, Hagenmuller P (1984) Z Anorg Allg Chem 517:43–58CrossRefGoogle Scholar
  22. 22.
    Tressaud A, Khairoun S, Grannec J, Dance JM, Hagenmuller P (1985) J Fluorine Chem 29:39CrossRefGoogle Scholar
  23. 23.
    Jasper SA, Huffman JC, Todd LJ (1998) Inorg Chem 37:6060–6064CrossRefGoogle Scholar
  24. 24.
    Eachus RS, Graves RE (1976) J Chem Phys 65:5445–5452CrossRefGoogle Scholar
  25. 25.
    Krigas T, Rogers MT (1971) J Chem Phys 54:4769–4775CrossRefGoogle Scholar
  26. 26.
    Raizman A, Barak J, Suss JT (1985) Phys Rev B 31:5716–5721CrossRefGoogle Scholar
  27. 27.
    Lane GA, Geiger WE, Connelly NG (1987) J Am Chem Soc 109:402–407CrossRefGoogle Scholar
  28. 28.
    Möller E, Kirmse R (1997) Inorg Chim Acta 257:273–276CrossRefGoogle Scholar
  29. 29.
    Luca V, Kukkadapu R, Kevan L (1991) J Chem Soc Faraday Trans 87:3083–3089CrossRefGoogle Scholar
  30. 30.
    Warren LF, Hawthorn MF (1968) J Am Chem Soc 90:4823–4828CrossRefGoogle Scholar
  31. 31.
    Kirmse R, Stach J, Dietzsch W, Steimecke G, Hoyer E (1980) Inorg Chem 19:2679–2685CrossRefGoogle Scholar
  32. 32.
    Pandey KK (1992) Coord Chem Rev 121:1–42CrossRefGoogle Scholar
  33. 33.
    Ray K, Weyhermüller T, Neese F, Wieghardt K (2005) Inorg Chem 44:5345–5360CrossRefGoogle Scholar
  34. 34.
    Motoyama T, Shimazaki Y, Yajima T, Nakabayashi Y, Naruta Y, Yamauchi O (2004) J Am Chem Soc 126:7378–7385CrossRefGoogle Scholar
  35. 35.
    Yamashita M, Takaishi S (2010) Chem Commun 46:4438–4448CrossRefGoogle Scholar
  36. 36.
    Takaishi S, Wu H, Xie J, Kajiwara T, Breedlove BK, Miyasaka H, Yamashita M (2010) Inorg Chem 49:3694–3696CrossRefGoogle Scholar
  37. 37.
    Blake AJ, Holder AJ, Hyde TI, Schröder M (1987) J Chem Soc Chem Commun 987–988Google Scholar
  38. 38.
    Blake AJ, Holder AJ, Hyde TI, Roberts YV, Lavery AJ, Schröder M (1987) J Organomet Chem 323:261–270CrossRefGoogle Scholar
  39. 39.
    Matsumoto M, Itoh M, Funahashi S, Takagi HD (1999) Can J Chem 77:1638–1647Google Scholar
  40. 40.
    Blake AJ, Gordon LM, Holder AJ, Hyde TI, Reid G, Schröder M (1988) J Chem Soc Chem Commun 1452–1454Google Scholar
  41. 41.
    McAuley A, Whitcombe TW (1988) Inorg Chem 27:3090–3099CrossRefGoogle Scholar
  42. 42.
    Hunter G, McAuley A, Whitcombe TW (1988) Inorg Chem 27:2634–2639CrossRefGoogle Scholar
  43. 43.
    Reid G, Blake AJ, Hyde TI, Schröder M (1988) J Chem Soc Chem Commun 1397–1399Google Scholar
  44. 44.
    Blake AJ, Reid G, Schröder M (1990) J Chem Soc Dalton Trans 3363–3373Google Scholar
  45. 45.
    Blake AJ, Crofts RD, de Groot B, Schröder M (1993) J Chem Soc Dalton Trans 485–486Google Scholar
  46. 46.
    Reid G, Schröder M (1990) Chem Soc Rev 19:239–269CrossRefGoogle Scholar
  47. 47.
    Hartwig JF (2010) Organotransition metal chemistry. University Science Books, Sausalito, CA, USAGoogle Scholar
  48. 48.
    Ackermann L, Vicente R, Kapdi AR (2009) Angew Chem Int Ed 48:9792–9826CrossRefGoogle Scholar
  49. 49.
    Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174–238CrossRefGoogle Scholar
  50. 50.
    Campeau LC, Fagnou K (2006) Chem Commun 1253–1264Google Scholar
  51. 51.
    McGlacken GP, Bateman LM (2009) Chem Soc Rev 38:2447–2464CrossRefGoogle Scholar
  52. 52.
    Pascual S, de Mendoza P, Echavarren AM (2007) Org Biomol Chem 5:2727–2734CrossRefGoogle Scholar
  53. 53.
    Stuart DR, Fagnou K (2007) Science 316:1172–1175CrossRefGoogle Scholar
  54. 54.
    Kalyani D, Sanford MS (2008) J Am Chem Soc 130:2150–2151CrossRefGoogle Scholar
  55. 55.
    Kalyani D, Satterfield AD, Sanford MS (2010) J Am Chem Soc 132:8419–8427CrossRefGoogle Scholar
  56. 56.
    Klein A, Niemeyer M (2000) Z Anorg Allg Chem 626:1191–1195CrossRefGoogle Scholar
  57. 57.
    Chen X, Goodhue CE, Yu JQ (2006) J Am Chem Soc 128:12634–12635CrossRefGoogle Scholar
  58. 58.
    Cho SH, Hwang SJ, Chang S (2008) J Am Chem Soc 130:9254–9256CrossRefGoogle Scholar
  59. 59.
    Stuart DR, Villemure E, Fagnou K (2007) J Am Chem Soc 129:12072–12073CrossRefGoogle Scholar
  60. 60.
    Takahashi M, Masui K, Sekiguchi H, Kobayashi N, Mori A, Funahashi M, Tamaoki N (2006) J Am Chem Soc 128:10930–10933CrossRefGoogle Scholar
  61. 61.
    Potavathri S, Dumas AS, Dwight TA, Naumiec GR, Hammann JM, DeBoef B (2008) Tetrahedron Lett 49:4050–4053CrossRefGoogle Scholar
  62. 62.
    Campeau LC, Parisien M, Jean A, Fagnou K (2006) J Am Chem Soc 128:581–590CrossRefGoogle Scholar
  63. 63.
    Lebrasseur N, Larrosa I (2008) J Am Chem Soc 130:2926–2927CrossRefGoogle Scholar
  64. 64.
    René O, Fagnou K (2010) Org Lett 12:2116–2119CrossRefGoogle Scholar
  65. 65.
    Seligson AL, Trogler WC (1992) J Am Chem Soc 114:7085–7089CrossRefGoogle Scholar
  66. 66.
    Kraatz HB, van der Boom ME, Ben-David Y, Milstein D (2001) Isr J Chem 41:163–171CrossRefGoogle Scholar
  67. 67.
    Ozawa F, Fujimori M, Yamamoto T, Yamamoto A (1986) Organometallics 5:2144–2149CrossRefGoogle Scholar
  68. 68.
    Lanci MP, Remy MS, Kaminsky W, Mayer JM, Sanford MS (2009) J Am Chem Soc 131:15618–15620CrossRefGoogle Scholar
  69. 69.
    Coronas JM, Muller G, Rocamora M (1986) J Organomet Chem 301:227–236CrossRefGoogle Scholar
  70. 70.
    Ceder RM, Granell J, Muller G, Font-Bardía M, Solans X (1996) Organometallics 15:4618–4624CrossRefGoogle Scholar
  71. 71.
    Higgs AT, Zinn PJ, Simmons SJ, Sanford MS (2009) Organometallics 28:6142–6144CrossRefGoogle Scholar
  72. 72.
    Tsou TT, Kochi JK (1979) J Am Chem Soc 101:7547–7560CrossRefGoogle Scholar
  73. 73.
    Matsunaga PT, Hillhouse GL, Rheingold AL (1993) J Am Chem Soc 115:2075–2077CrossRefGoogle Scholar
  74. 74.
    Koo K, Hillhouse GL (1995) Organometallics 14:4421–4423CrossRefGoogle Scholar
  75. 75.
    Higgs AT, Zinn PJ, Sanford MS (2010) Organometallics 29:5446–5449Google Scholar
  76. 76.
    Johansson L, Ryan OB, Rømming C, Tilset M (1998) Organometallics 17:3957–3966CrossRefGoogle Scholar
  77. 77.
    Mei TS, Wang X, Yu JQ (2009) J Am Chem Soc 131:10806–10807CrossRefGoogle Scholar
  78. 78.
    Neumann JJ, Rakshit S, Dröge T, Glorius F (2009) Angew Chem Int Ed 48:6892–6895CrossRefGoogle Scholar
  79. 79.
    Manolikakes G, Knochel P (2009) Angew Chem Int Ed 48:205–209CrossRefGoogle Scholar
  80. 80.
    Kienle M, Knochel P (2010) Org Lett 12:2702–2705CrossRefGoogle Scholar
  81. 81.
    Kramer AV, Labinger JA, Bradley JS, Osborn JA (1974) J Am Chem Soc 96:7145–7147CrossRefGoogle Scholar
  82. 82.
    Kramer AV, Osborn JA (1974) J Am Chem Soc 96:7832–7833CrossRefGoogle Scholar
  83. 83.
    Boisvert L, Denney MC, Hanson SK, Goldberg KI (2009) J Am Chem Soc 131:15802–15814CrossRefGoogle Scholar
  84. 84.
    Kamaraj K, Bandyopadhyay D (1999) Organometallics 18:438–446CrossRefGoogle Scholar
  85. 85.
    Khusnutdinova JR, Rath NP, Mirica LM (2010) J Am Chem Soc 132:7303–7305CrossRefGoogle Scholar
  86. 86.
    Cotton FA, Murillo CA, Walton RA (eds) (2005) Multiple bonds between metal atoms. Springer Science and Business Media, New YorkGoogle Scholar
  87. 87.
    Cotton FA, Matusz M, Poli R, Feng X (1988) J Am Chem Soc 110:1144–1154CrossRefGoogle Scholar
  88. 88.
    Bercaw JE, Durrell AC, Gray HB, Green JC, Hazari N, Labinger JA, Winkler JR (2010) Inorg Chem 49:1801–1810CrossRefGoogle Scholar
  89. 89.
    Xia BH, Che CM, Zhou ZY (2003) Chem Eur J 9:3055–3064CrossRefGoogle Scholar
  90. 90.
    Pan QJ, Zhang HX, Zhou X, Fu HG, Yu HT (2007) J Phys Chem A 111:287–294CrossRefGoogle Scholar
  91. 91.
    Yip HK, Lai TF, Che CM (1991) J Chem Soc Dalton Trans 1639–1641Google Scholar
  92. 92.
    Berry JF, Cotton FA, Ibragimov SA, Murillo CA, Wang X (2005) Inorg Chem 44:6129–6137CrossRefGoogle Scholar
  93. 93.
    Cotton FA, Matusz M, Poli R (1987) Inorg Chem 26:1472–1474CrossRefGoogle Scholar
  94. 94.
    Berry JF, Bill E, Bothe E, Cotton FA, Dalal NS, Ibragimov SA, Kaur N, Liu CY, Murillo CA, Nellutla S, North JM, Villagrán D (2007) J Am Chem Soc 129:1393–1401CrossRefGoogle Scholar
  95. 95.
    Yao CL, He LP, Korp JD, Bear JL (1988) Inorg Chem 27:4389–4395CrossRefGoogle Scholar
  96. 96.
    Powers DC, Ritter T (2009) Nat Chem 1:302–309CrossRefGoogle Scholar
  97. 97.
    Cotton FA, Gu J, Murillo CA, Timmons DJ (1998) J Am Chem Soc 120:13280–13281CrossRefGoogle Scholar
  98. 98.
    Cotton FA, Koshevoy IO, Lahuerta P, Murillo CA, Sanaú M, Ubeda MA, Zhao Q (2006) J Am Chem Soc 128:13674–13675CrossRefGoogle Scholar
  99. 99.
    Penno D, Lillo V, Koshevoy IO, Sanaú M, Ubeda MA, Lahuerta P, Fernández E (2008) Chem Eur J 14:10648–10655CrossRefGoogle Scholar
  100. 100.
    Davidson JM, Triggs C (1966) Chem Ind (Lond) 457Google Scholar
  101. 101.
    Tisue T, Downs WJ (1969) J Chem Soc D 410aGoogle Scholar
  102. 102.
    Henry PM (1971) J Org Chem 36:1886–1890CrossRefGoogle Scholar
  103. 103.
    Stock LM, Tse K, Vorvick LJ, Walstrum SA (1981) J Org Chem 46:1757–1759CrossRefGoogle Scholar
  104. 104.
    Yoneyama T, Crabtree RH (1996) J Mol Catal A Chem 108:35–40CrossRefGoogle Scholar
  105. 105.
    Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300–2301CrossRefGoogle Scholar
  106. 106.
    Desai LV, Hull KL, Sanford MS (2004) J Am Chem Soc 126:9542–9543CrossRefGoogle Scholar
  107. 107.
    Dick AR, Kampf JW, Sanford MS (2005) J Am Chem Soc 127:12790–12791CrossRefGoogle Scholar
  108. 108.
    Racowski JM, Dick AR, Sanford MS (2009) J Am Chem Soc 131:10974–10983CrossRefGoogle Scholar
  109. 109.
    Powers DC, Geibel MAL, Klein JEMN, Ritter T (2009) J Am Chem Soc 131:17050–17051CrossRefGoogle Scholar
  110. 110.
    Gutierrez MA, Newkome GR, Selbin J (1980) J Organomet Chem 202:341–350CrossRefGoogle Scholar
  111. 111.
    Dinçer M, Özdemir N, Günay ME, Çetinkaya B (2008) Acta Crystallogr E Struct Rep Online 64:M381CrossRefGoogle Scholar
  112. 112.
    Fahey DR (1970) J Chem Soc D 417Google Scholar
  113. 113.
    Fahey DR (1971) J Organomet Chem 27:283–292CrossRefGoogle Scholar
  114. 114.
    Whitfield SR, Sanford MS (2007) J Am Chem Soc 129:15142–15143CrossRefGoogle Scholar
  115. 115.
    Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Org Lett 8:2523–2526CrossRefGoogle Scholar
  116. 116.
    Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Tetrahedron 62:11483–11498CrossRefGoogle Scholar
  117. 117.
    Powers DC, Xiao DY, Geibel MAL, Ritter T (2010) J Am Chem Soc 132:14530–14536CrossRefGoogle Scholar
  118. 118.
    Deprez NR, Sanford MS (2009) J Am Chem Soc 131:11234–11241CrossRefGoogle Scholar
  119. 119.
    Powers DC, Benitez D, Tkatchouk E, Goddard WA, Ritter T (2010) J Am Chem Soc 132:14092–14103CrossRefGoogle Scholar
  120. 120.
    Riggs WM (1972) Anal Chem 44:830–832CrossRefGoogle Scholar
  121. 121.
    Leigh GJ (1975) Inorg Chim Acta 14:L35–L36CrossRefGoogle Scholar
  122. 122.
    Chatt J, Elson CM, Hooper NE, Leigh GJ (1975) J Chem Soc Dalton Trans 2392–2401Google Scholar
  123. 123.
    Cisar A, Corbett JD, Daake RL (1979) Inorg Chem 18:836–843CrossRefGoogle Scholar
  124. 124.
    Corbett JD (1983) Inorg Chem 22:2669–2672CrossRefGoogle Scholar
  125. 125.
    Lyons TW, Sanford MS (2010) Chem Rev 110:1147–1169CrossRefGoogle Scholar
  126. 126.
    Xu L-M, Li B-J, Yang Z, Shi Z-J (2010) Chem Soc Rev 712–733Google Scholar
  127. 127.
    Muñiz K (2009) Angew Chem Int Ed 48:9412–9423CrossRefGoogle Scholar
  128. 128.
    Chen X, Engle KM, Wang DH, Yu JQ (2009) Angew Chem Int Ed 48:5094–5115CrossRefGoogle Scholar
  129. 129.
    Canty AJ (1992) Acc Chem Res 25:83–90CrossRefGoogle Scholar
  130. 130.
    Byers PK, Canty AJ, Crespo M, Puddephatt RJ, Scott JD (1988) Organometallics 7:1363–1367CrossRefGoogle Scholar
  131. 131.
    Fu Y, Li Z, Liang S, Guo QX, Liu L (2008) Organometallics 27:3736–3742CrossRefGoogle Scholar
  132. 132.
    Furuya T, Benitez D, Tkatchouk E, Strom AE, Tang P, Goddard WA, Ritter T (2010) J Am Chem Soc 132:3793–3807CrossRefGoogle Scholar
  133. 133.
    Stowers KJ, Sanford MS (2009) Org Lett 11:4584–4587CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2011

Authors and Affiliations

  1. 1.Department of Chemistry and Chemical BiologyHarvard UniversityCambridgeUSA

Personalised recommendations