Skip to main content
SpringerLink
Log in

Palladium(III) in Synthesis and Catalysis

  • Chapter
  • First Online:
Book cover Higher Oxidation State Organopalladium and Platinum Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 35))

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

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 129.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
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. Negishi E (ed) (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley, New York

    Google Scholar 

  2. Murahashi T, Kurosawa H (2002) Coord Chem Rev 231:207–228

    Article  CAS  Google Scholar 

  3. Markert C, Neuburger M, Kulicke K, Meuwly M, Pfaltz A (2007) Angew Chem Int Ed 46:5892–5895

    Article  CAS  Google Scholar 

  4. Hama T, Hartwig JF (2008) Org Lett 10:1545–1548

    Article  CAS  Google Scholar 

  5. Albright TA (1982) Tetrahedron 38:1339–1388

    Article  CAS  Google Scholar 

  6. Miessler GL, Tarr DA (2004) Inorganic chemistry. Pearson Education, Upper Saddle River, New Jersey

    Google Scholar 

  7. Canty AJ, Gardiner MG, Jones RC, Rodemann T, Sharma M (2009) J Am Chem Soc 131:7236–7237

    Article  CAS  Google Scholar 

  8. Bonnington KJ, Jennings MC, Puddephatt RJ (2008) Organometallics 27:6521–6530

    Article  CAS  Google Scholar 

  9. Roundhill DM, Gray HB, Che CM (1989) Acc Chem Res 22:55–61

    Article  CAS  Google Scholar 

  10. Matsumoto K, Sakai K (2000) Adv Inorg Chem 49:375–427

    Article  CAS  Google Scholar 

  11. Lippert B (1999) Coord Chem Rev 182:263–295

    Article  Google Scholar 

  12. Zipp AP (1988) Coord Chem Rev 84:47–83

    Article  CAS  Google Scholar 

  13. Blake AJ, Gould RO, Holder AJ, Hyde TI, Lavery AJ, Odulate MO, Schröder M (1987) J Chem Soc Chem Commun 118–120

    Google Scholar 

  14. Usón R, Forniés J, Tomás M, Menjón B, Sünkel K, Bau R (1984) J Chem Soc Chem Commun 751–752

    Google Scholar 

  15. Usón R, Forniés J, Tomás M, Menjón B, Bau R, Sünkel K, Kuwabara E (1986) Organometallics 5:1576–1581

    Article  Google Scholar 

  16. Nyholm RS, Sharpe AG (1952) J Chem Soc 3579–3587

    Google Scholar 

  17. Sharpe AG (1950) J Chem Soc 3444–3450

    Google Scholar 

  18. Bartlett N, Rao PR (1964) Proc Chem Soc Lond 393–394

    Google Scholar 

  19. Tressaud A, Wintenberger M, Bartlett N, Hagenmuller P (1976) C R Acad Sci Paris 282:1069–1072

    CAS  Google Scholar 

  20. Tressaud A, Khairoun S, Dance JM, Grannec J, Portier J, Hagenmuller P (1982) J Fluorine Chem 21:28

    Article  Google Scholar 

  21. Tressaud A, Khairoun S, Dance JM, Hagenmuller P (1984) Z Anorg Allg Chem 517:43–58

    Article  CAS  Google Scholar 

  22. Tressaud A, Khairoun S, Grannec J, Dance JM, Hagenmuller P (1985) J Fluorine Chem 29:39

    Article  Google Scholar 

  23. Jasper SA, Huffman JC, Todd LJ (1998) Inorg Chem 37:6060–6064

    Article  CAS  Google Scholar 

  24. Eachus RS, Graves RE (1976) J Chem Phys 65:5445–5452

    Article  CAS  Google Scholar 

  25. Krigas T, Rogers MT (1971) J Chem Phys 54:4769–4775

    Article  CAS  Google Scholar 

  26. Raizman A, Barak J, Suss JT (1985) Phys Rev B 31:5716–5721

    Article  CAS  Google Scholar 

  27. Lane GA, Geiger WE, Connelly NG (1987) J Am Chem Soc 109:402–407

    Article  CAS  Google Scholar 

  28. Möller E, Kirmse R (1997) Inorg Chim Acta 257:273–276

    Article  Google Scholar 

  29. Luca V, Kukkadapu R, Kevan L (1991) J Chem Soc Faraday Trans 87:3083–3089

    Article  CAS  Google Scholar 

  30. Warren LF, Hawthorn MF (1968) J Am Chem Soc 90:4823–4828

    Article  CAS  Google Scholar 

  31. Kirmse R, Stach J, Dietzsch W, Steimecke G, Hoyer E (1980) Inorg Chem 19:2679–2685

    Article  CAS  Google Scholar 

  32. Pandey KK (1992) Coord Chem Rev 121:1–42

    Article  CAS  Google Scholar 

  33. Ray K, Weyhermüller T, Neese F, Wieghardt K (2005) Inorg Chem 44:5345–5360

    Article  CAS  Google Scholar 

  34. Motoyama T, Shimazaki Y, Yajima T, Nakabayashi Y, Naruta Y, Yamauchi O (2004) J Am Chem Soc 126:7378–7385

    Article  CAS  Google Scholar 

  35. Yamashita M, Takaishi S (2010) Chem Commun 46:4438–4448

    Article  CAS  Google Scholar 

  36. Takaishi S, Wu H, Xie J, Kajiwara T, Breedlove BK, Miyasaka H, Yamashita M (2010) Inorg Chem 49:3694–3696

    Article  CAS  Google Scholar 

  37. Blake AJ, Holder AJ, Hyde TI, Schröder M (1987) J Chem Soc Chem Commun 987–988

    Google Scholar 

  38. Blake AJ, Holder AJ, Hyde TI, Roberts YV, Lavery AJ, Schröder M (1987) J Organomet Chem 323:261–270

    Article  CAS  Google Scholar 

  39. Matsumoto M, Itoh M, Funahashi S, Takagi HD (1999) Can J Chem 77:1638–1647

    CAS  Google Scholar 

  40. Blake AJ, Gordon LM, Holder AJ, Hyde TI, Reid G, Schröder M (1988) J Chem Soc Chem Commun 1452–1454

    Google Scholar 

  41. McAuley A, Whitcombe TW (1988) Inorg Chem 27:3090–3099

    Article  CAS  Google Scholar 

  42. Hunter G, McAuley A, Whitcombe TW (1988) Inorg Chem 27:2634–2639

    Article  CAS  Google Scholar 

  43. Reid G, Blake AJ, Hyde TI, Schröder M (1988) J Chem Soc Chem Commun 1397–1399

    Google Scholar 

  44. Blake AJ, Reid G, Schröder M (1990) J Chem Soc Dalton Trans 3363–3373

    Google Scholar 

  45. Blake AJ, Crofts RD, de Groot B, Schröder M (1993) J Chem Soc Dalton Trans 485–486

    Google Scholar 

  46. Reid G, Schröder M (1990) Chem Soc Rev 19:239–269

    Article  CAS  Google Scholar 

  47. Hartwig JF (2010) Organotransition metal chemistry. University Science Books, Sausalito, CA, USA

    Google Scholar 

  48. Ackermann L, Vicente R, Kapdi AR (2009) Angew Chem Int Ed 48:9792–9826

    Article  CAS  Google Scholar 

  49. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174–238

    Article  CAS  Google Scholar 

  50. Campeau LC, Fagnou K (2006) Chem Commun 1253–1264

    Google Scholar 

  51. McGlacken GP, Bateman LM (2009) Chem Soc Rev 38:2447–2464

    Article  CAS  Google Scholar 

  52. Pascual S, de Mendoza P, Echavarren AM (2007) Org Biomol Chem 5:2727–2734

    Article  CAS  Google Scholar 

  53. Stuart DR, Fagnou K (2007) Science 316:1172–1175

    Article  CAS  Google Scholar 

  54. Kalyani D, Sanford MS (2008) J Am Chem Soc 130:2150–2151

    Article  CAS  Google Scholar 

  55. Kalyani D, Satterfield AD, Sanford MS (2010) J Am Chem Soc 132:8419–8427

    Article  CAS  Google Scholar 

  56. Klein A, Niemeyer M (2000) Z Anorg Allg Chem 626:1191–1195

    Article  CAS  Google Scholar 

  57. Chen X, Goodhue CE, Yu JQ (2006) J Am Chem Soc 128:12634–12635

    Article  CAS  Google Scholar 

  58. Cho SH, Hwang SJ, Chang S (2008) J Am Chem Soc 130:9254–9256

    Article  CAS  Google Scholar 

  59. Stuart DR, Villemure E, Fagnou K (2007) J Am Chem Soc 129:12072–12073

    Article  CAS  Google Scholar 

  60. Takahashi M, Masui K, Sekiguchi H, Kobayashi N, Mori A, Funahashi M, Tamaoki N (2006) J Am Chem Soc 128:10930–10933

    Article  CAS  Google Scholar 

  61. Potavathri S, Dumas AS, Dwight TA, Naumiec GR, Hammann JM, DeBoef B (2008) Tetrahedron Lett 49:4050–4053

    Article  CAS  Google Scholar 

  62. Campeau LC, Parisien M, Jean A, Fagnou K (2006) J Am Chem Soc 128:581–590

    Article  CAS  Google Scholar 

  63. Lebrasseur N, Larrosa I (2008) J Am Chem Soc 130:2926–2927

    Article  CAS  Google Scholar 

  64. René O, Fagnou K (2010) Org Lett 12:2116–2119

    Article  CAS  Google Scholar 

  65. Seligson AL, Trogler WC (1992) J Am Chem Soc 114:7085–7089

    Article  CAS  Google Scholar 

  66. Kraatz HB, van der Boom ME, Ben-David Y, Milstein D (2001) Isr J Chem 41:163–171

    Article  CAS  Google Scholar 

  67. Ozawa F, Fujimori M, Yamamoto T, Yamamoto A (1986) Organometallics 5:2144–2149

    Article  CAS  Google Scholar 

  68. Lanci MP, Remy MS, Kaminsky W, Mayer JM, Sanford MS (2009) J Am Chem Soc 131:15618–15620

    Article  CAS  Google Scholar 

  69. Coronas JM, Muller G, Rocamora M (1986) J Organomet Chem 301:227–236

    Article  CAS  Google Scholar 

  70. Ceder RM, Granell J, Muller G, Font-Bardía M, Solans X (1996) Organometallics 15:4618–4624

    Article  CAS  Google Scholar 

  71. Higgs AT, Zinn PJ, Simmons SJ, Sanford MS (2009) Organometallics 28:6142–6144

    Article  CAS  Google Scholar 

  72. Tsou TT, Kochi JK (1979) J Am Chem Soc 101:7547–7560

    Article  CAS  Google Scholar 

  73. Matsunaga PT, Hillhouse GL, Rheingold AL (1993) J Am Chem Soc 115:2075–2077

    Article  CAS  Google Scholar 

  74. Koo K, Hillhouse GL (1995) Organometallics 14:4421–4423

    Article  CAS  Google Scholar 

  75. Higgs AT, Zinn PJ, Sanford MS (2010) Organometallics 29:5446–5449

    Google Scholar 

  76. Johansson L, Ryan OB, Rømming C, Tilset M (1998) Organometallics 17:3957–3966

    Article  CAS  Google Scholar 

  77. Mei TS, Wang X, Yu JQ (2009) J Am Chem Soc 131:10806–10807

    Article  CAS  Google Scholar 

  78. Neumann JJ, Rakshit S, Dröge T, Glorius F (2009) Angew Chem Int Ed 48:6892–6895

    Article  CAS  Google Scholar 

  79. Manolikakes G, Knochel P (2009) Angew Chem Int Ed 48:205–209

    Article  CAS  Google Scholar 

  80. Kienle M, Knochel P (2010) Org Lett 12:2702–2705

    Article  CAS  Google Scholar 

  81. Kramer AV, Labinger JA, Bradley JS, Osborn JA (1974) J Am Chem Soc 96:7145–7147

    Article  CAS  Google Scholar 

  82. Kramer AV, Osborn JA (1974) J Am Chem Soc 96:7832–7833

    Article  CAS  Google Scholar 

  83. Boisvert L, Denney MC, Hanson SK, Goldberg KI (2009) J Am Chem Soc 131:15802–15814

    Article  CAS  Google Scholar 

  84. Kamaraj K, Bandyopadhyay D (1999) Organometallics 18:438–446

    Article  CAS  Google Scholar 

  85. Khusnutdinova JR, Rath NP, Mirica LM (2010) J Am Chem Soc 132:7303–7305

    Article  CAS  Google Scholar 

  86. Cotton FA, Murillo CA, Walton RA (eds) (2005) Multiple bonds between metal atoms. Springer Science and Business Media, New York

    Google Scholar 

  87. Cotton FA, Matusz M, Poli R, Feng X (1988) J Am Chem Soc 110:1144–1154

    Article  CAS  Google Scholar 

  88. Bercaw JE, Durrell AC, Gray HB, Green JC, Hazari N, Labinger JA, Winkler JR (2010) Inorg Chem 49:1801–1810

    Article  CAS  Google Scholar 

  89. Xia BH, Che CM, Zhou ZY (2003) Chem Eur J 9:3055–3064

    Article  CAS  Google Scholar 

  90. Pan QJ, Zhang HX, Zhou X, Fu HG, Yu HT (2007) J Phys Chem A 111:287–294

    Article  CAS  Google Scholar 

  91. Yip HK, Lai TF, Che CM (1991) J Chem Soc Dalton Trans 1639–1641

    Google Scholar 

  92. Berry JF, Cotton FA, Ibragimov SA, Murillo CA, Wang X (2005) Inorg Chem 44:6129–6137

    Article  CAS  Google Scholar 

  93. Cotton FA, Matusz M, Poli R (1987) Inorg Chem 26:1472–1474

    Article  CAS  Google Scholar 

  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 129:1393–1401

    Article  CAS  Google Scholar 

  95. Yao CL, He LP, Korp JD, Bear JL (1988) Inorg Chem 27:4389–4395

    Article  CAS  Google Scholar 

  96. Powers DC, Ritter T (2009) Nat Chem 1:302–309

    Article  CAS  Google Scholar 

  97. Cotton FA, Gu J, Murillo CA, Timmons DJ (1998) J Am Chem Soc 120:13280–13281

    Article  CAS  Google Scholar 

  98. Cotton FA, Koshevoy IO, Lahuerta P, Murillo CA, Sanaú M, Ubeda MA, Zhao Q (2006) J Am Chem Soc 128:13674–13675

    Article  CAS  Google Scholar 

  99. Penno D, Lillo V, Koshevoy IO, Sanaú M, Ubeda MA, Lahuerta P, Fernández E (2008) Chem Eur J 14:10648–10655

    Article  CAS  Google Scholar 

  100. Davidson JM, Triggs C (1966) Chem Ind (Lond) 457

    Google Scholar 

  101. Tisue T, Downs WJ (1969) J Chem Soc D 410a

    Google Scholar 

  102. Henry PM (1971) J Org Chem 36:1886–1890

    Article  CAS  Google Scholar 

  103. Stock LM, Tse K, Vorvick LJ, Walstrum SA (1981) J Org Chem 46:1757–1759

    Article  CAS  Google Scholar 

  104. Yoneyama T, Crabtree RH (1996) J Mol Catal A Chem 108:35–40

    Article  CAS  Google Scholar 

  105. Dick AR, Hull KL, Sanford MS (2004) J Am Chem Soc 126:2300–2301

    Article  CAS  Google Scholar 

  106. Desai LV, Hull KL, Sanford MS (2004) J Am Chem Soc 126:9542–9543

    Article  CAS  Google Scholar 

  107. Dick AR, Kampf JW, Sanford MS (2005) J Am Chem Soc 127:12790–12791

    Article  CAS  Google Scholar 

  108. Racowski JM, Dick AR, Sanford MS (2009) J Am Chem Soc 131:10974–10983

    Article  CAS  Google Scholar 

  109. Powers DC, Geibel MAL, Klein JEMN, Ritter T (2009) J Am Chem Soc 131:17050–17051

    Article  CAS  Google Scholar 

  110. Gutierrez MA, Newkome GR, Selbin J (1980) J Organomet Chem 202:341–350

    Article  CAS  Google Scholar 

  111. Dinçer M, Özdemir N, Günay ME, Çetinkaya B (2008) Acta Crystallogr E Struct Rep Online 64:M381

    Article  CAS  Google Scholar 

  112. Fahey DR (1970) J Chem Soc D 417

    Google Scholar 

  113. Fahey DR (1971) J Organomet Chem 27:283–292

    Article  CAS  Google Scholar 

  114. Whitfield SR, Sanford MS (2007) J Am Chem Soc 129:15142–15143

    Article  CAS  Google Scholar 

  115. Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Org Lett 8:2523–2526

    Article  CAS  Google Scholar 

  116. Kalyani D, Dick AR, Anani WQ, Sanford MS (2006) Tetrahedron 62:11483–11498

    Article  CAS  Google Scholar 

  117. Powers DC, Xiao DY, Geibel MAL, Ritter T (2010) J Am Chem Soc 132:14530–14536

    Article  CAS  Google Scholar 

  118. Deprez NR, Sanford MS (2009) J Am Chem Soc 131:11234–11241

    Article  CAS  Google Scholar 

  119. Powers DC, Benitez D, Tkatchouk E, Goddard WA, Ritter T (2010) J Am Chem Soc 132:14092–14103

    Article  CAS  Google Scholar 

  120. Riggs WM (1972) Anal Chem 44:830–832

    Article  CAS  Google Scholar 

  121. Leigh GJ (1975) Inorg Chim Acta 14:L35–L36

    Article  CAS  Google Scholar 

  122. Chatt J, Elson CM, Hooper NE, Leigh GJ (1975) J Chem Soc Dalton Trans 2392–2401

    Google Scholar 

  123. Cisar A, Corbett JD, Daake RL (1979) Inorg Chem 18:836–843

    Article  CAS  Google Scholar 

  124. Corbett JD (1983) Inorg Chem 22:2669–2672

    Article  CAS  Google Scholar 

  125. Lyons TW, Sanford MS (2010) Chem Rev 110:1147–1169

    Article  CAS  Google Scholar 

  126. Xu L-M, Li B-J, Yang Z, Shi Z-J (2010) Chem Soc Rev 712–733

    Google Scholar 

  127. Muñiz K (2009) Angew Chem Int Ed 48:9412–9423

    Article  CAS  Google Scholar 

  128. Chen X, Engle KM, Wang DH, Yu JQ (2009) Angew Chem Int Ed 48:5094–5115

    Article  CAS  Google Scholar 

  129. Canty AJ (1992) Acc Chem Res 25:83–90

    Article  CAS  Google Scholar 

  130. Byers PK, Canty AJ, Crespo M, Puddephatt RJ, Scott JD (1988) Organometallics 7:1363–1367

    Article  CAS  Google Scholar 

  131. Fu Y, Li Z, Liang S, Guo QX, Liu L (2008) Organometallics 27:3736–3742

    Article  CAS  Google Scholar 

  132. Furuya T, Benitez D, Tkatchouk E, Strom AE, Tang P, Goddard WA, Ritter T (2010) J Am Chem Soc 132:3793–3807

    Article  CAS  Google Scholar 

  133. Stowers KJ, Sanford MS (2009) Org Lett 11:4584–4587

    Article  CAS  Google Scholar 

Download references

Acknowledgment

We gratefully acknowledge financial support for this work from the NIH-NIGMS (GM088237) and the NSF (CHE-0952753). TR is a Sloan Fellow.

Author information

Authors and Affiliations

  1. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA, 02138, USA

    David C. Powers & Tobias Ritter

Authors
  1. David C. Powers
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tobias Ritter
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tobias Ritter .

Editor information

Editors and Affiliations

  1. , School of Chemistry, University of Tasmania, Private Bag 75, Hobart, 7001, Tasmania, Australia

    Allan J. Canty

Rights and permissions

Reprints and permissions

Copyright information

© 2011 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Powers, D.C., Ritter, T. (2011). Palladium(III) in Synthesis and Catalysis. In: Canty, A. (eds) Higher Oxidation State Organopalladium and Platinum Chemistry. Topics in Organometallic Chemistry, vol 35. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-17429-2_6

Download citation

Publish with us

Policies and ethics

Search

Navigation