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Reactivities and Electronic Properties of Boryl Ligands

  • Zhenyang LinEmail author
Chapter
Part of the Structure and Bonding book series (STRUCTURE, volume 167)

Abstract

Transition metal boryl complexes play an important role as reactive intermediates in many catalytic processes. The reactivities and electronic properties of boryl ligands, in particular their nucleophilic and electrophilic behaviors, are discussed and reviewed in this article.

Keywords

Boryl complexes Boryl ligands Borylation Structure and bonding 

Notes

Acknowledgments

I thank my co-workers Li Dang, Wai Han Lam, King Chung Lam, Haitao Zhao, and Jun Zhu for their contribution to the research reported here. I am particularly grateful to Professor Todd B. Marder, my experimental collaborator, for his insightful comments and suggestions on the boryl chemistry discussed in this article. I would also like to thank Professor Holger Braunschweig and Dr. Rian Dewhurst for their valuable comments. I also want to acknowledge financial support from the Hong Kong Research Grants Council (Grant Nos. HKUST 603711, 603313 and CUHK7/CRF/12G).

References

  1. 1.
    Baker RT, Ovenall DW, Calabrese JC, Westcott SA, Taylor NJ, Williams ID, Marder TB (1990) J Am Chem Soc 112:9399CrossRefGoogle Scholar
  2. 2.
    Knorr JR, Merola JS (1990) Organometallics 9:3008CrossRefGoogle Scholar
  3. 3.
    Hartwig JF, Waltz KM, Muhoro CN, He X, Eisenstein O, Bosque R, Maseras F (1997) In: Siebert W (ed) Advances in boron chemistry. The Royal Society of Chemistry, Cambridge, p 373Google Scholar
  4. 4.
    Wadepohl H (1997) Angew Chem Int Ed 36:2441CrossRefGoogle Scholar
  5. 5.
    Irvine GJ, Lesley MJG, Marder TB, Norman NC, Rice CR, Robins EG, Roper WR, Whittell GR, Wright LJ (1998) Chem Rev 98:2685CrossRefGoogle Scholar
  6. 6.
    Braunschweig H (1998) Angew Chem Int Ed 37:1786CrossRefGoogle Scholar
  7. 7.
    Smith MR (1999) Prog Inorg Chem 48:505CrossRefGoogle Scholar
  8. 8.
    Braunschweig H, Colling M (2001) Coord Chem Rev 223:1CrossRefGoogle Scholar
  9. 9.
    Coombs DL, Aldridge S (2004) Coord Chem Rev 248:535CrossRefGoogle Scholar
  10. 10.
    Braunschweig H, Whittell G (2005) Chem Eur J 11:6128CrossRefGoogle Scholar
  11. 11.
    Braunschweig H, Kollann C, Rais D (2006) Angew Chem Int Ed 45:5254CrossRefGoogle Scholar
  12. 12.
    Marder TB (2008) In: Fairlamb IJS, Lynam JM (eds) Specialist periodical reports: organometallic chemistry, vol 34. Royal Society of Chemistry, Cambridge, p 46Google Scholar
  13. 13.
    Kays DL, Aldridge S (2008) Struct Bonding (Berlin) 130:29CrossRefGoogle Scholar
  14. 14.
    Dang L, Lin ZY, Marder TB (2009) Chem Commun 3987Google Scholar
  15. 15.
    Mkhalid IA, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2010) Chem Rev 110:890CrossRefGoogle Scholar
  16. 16.
    Braunschweig H, Dewhurst RD, Schneider A (2010) Chem Rev 110:3924CrossRefGoogle Scholar
  17. 17.
    Braunschweig H, Dörfler R, Mies J, Oechsner A (2011) Chem Eur J 17:12101CrossRefGoogle Scholar
  18. 18.
    Cid J, Gulyás H, Carbó JJ, Fernández E (2012) Chem Soc Rev 41:3558CrossRefGoogle Scholar
  19. 19.
    Lillo V, Bonet A, Fernández E (2009) Dalton Trans 2899Google Scholar
  20. 20.
    Rablen PR, Hartwig JF, Nolan SP (1994) J Am Chem Soc 116:4121CrossRefGoogle Scholar
  21. 21.
    Sakaki S, Kai S, Sugimoto M (1999) Organometallics 18:4825CrossRefGoogle Scholar
  22. 22.
    Giju KT, Bickelhaupt FM, Frenking G (2000) Inorg Chem 39:4776CrossRefGoogle Scholar
  23. 23.
    Sivignon G, Fleurat-Lassard P, Onno JM, Volatron F (2002) Inorg Chem 41:6656CrossRefGoogle Scholar
  24. 24.
    Dickinson AA, Willock DJ, Calder RJ, Aldridge S (2002) Organometallics 21:1146CrossRefGoogle Scholar
  25. 25.
    Cundari TR, Zhao Y (2003) Inorg Chim Acta 345:70CrossRefGoogle Scholar
  26. 26.
    Lam WH, Shimada S, Batsanov AS, Lin Z, Marder TB, Cowan J, Howard JAK, Mason SA, McIntyre GJ (2003) Organometallics 22:4557CrossRefGoogle Scholar
  27. 27.
    Zhu J, Lin Z, Marder TB (2005) Inorg Chem 44:9384CrossRefGoogle Scholar
  28. 28.
    Braunschweig H, Brenner HP, Müller A, Radacki K, Rais D, Uttinger K (2007) Chem Eur J 13:7171CrossRefGoogle Scholar
  29. 29.
    Souza FES, Nguyen P, Marder TB, Scott AJ, Clegg W (2005) Inorg Chim Acta 358:1501Google Scholar
  30. 30.
    Westcott SA, Marder TB, Baker RT, Calabrese JC (1993) Can J Chem 71:930CrossRefGoogle Scholar
  31. 31.
    Clegg W, Lawlor FJ, Lesley G, Marder TB, Norman NC, Orpen AG, Quayle MJ, Rice CR, Scott AJ, Souza FE (1988) J Organomet Chem 550:183CrossRefGoogle Scholar
  32. 32.
    Lesley G, Nguyen P, Taylor NJ, Marder TB, Scott AJ, Clegg W, Norman NC (1996) Organometallics 15:5137CrossRefGoogle Scholar
  33. 33.
    Braunschweig H, Leech R, Rais D, Radacki K, Uttinger K (2008) Organometallics 27:418CrossRefGoogle Scholar
  34. 34.
    Braunschweig H, Gruss K, Radacki K, Uttinger K (2008) Eur J Inorg Chem 1462Google Scholar
  35. 35.
    Braunschweig H, Fuβ M, Radacki K, Uttinger K (2009) Z Anorg Allg Chem 635:208CrossRefGoogle Scholar
  36. 36.
    Braunschweig H, Damme A, Kupfer T (2011) Angew Chem Int Ed 50:7179CrossRefGoogle Scholar
  37. 37.
    Bauer J, Braunschweig H, Kraft K, Radacki K (2011) Angew Chem Int Ed 50:10457CrossRefGoogle Scholar
  38. 38.
    Braunschweig H, Radacki K, Uttinger K (2008) Eur Chem J 14:7858CrossRefGoogle Scholar
  39. 39.
    Braunschweig H, Damme A, Kupfer T (2012) Eur Chem J 18:15927CrossRefGoogle Scholar
  40. 40.
    Arnold N, Braunschweig H, Brenner P, Jimenez-Halla JOC, Kupfer T, Radacki K (2012) Organometallics 31:1897CrossRefGoogle Scholar
  41. 41.
    Ishiyama T, Yamamoto M, Miyaura N (1996) Chem Lett 1117Google Scholar
  42. 42.
    Iverson CN, Smith MR III (1995) J Am Chem Soc 117:4403CrossRefGoogle Scholar
  43. 43.
    Clegg W, Johann T, Marder TB, Norman NC, Orpen AG, Peakman T, Quayle MJ, Rice CR, Scott AJ (1998) J Chem Soc Dalton Trans 1431Google Scholar
  44. 44.
    Charmant JPH, Fan C, Norman NC, Pringle PG (2007) Dalton Trans 114Google Scholar
  45. 45.
    Braunschweig H, Brenner P, Dewhurst RD, Güthlein F, Jimenez-Halla JOC, Radacki K, Wolf J, Zöllner L (2012) Chem Eur J 18:8605CrossRefGoogle Scholar
  46. 46.
    Braunschweig H, Bertermann R, Brenner P, Burzler M, Dewhurst RD, Radacki K, Seeler F (2011) Chem Eur J 17:11828CrossRefGoogle Scholar
  47. 47.
    Hartwig JF, Muhoro CN, He X, Eisenstein O, Bosque R, Maseras F (1996) J Am Chem Soc 118:10936CrossRefGoogle Scholar
  48. 48.
    Lam WH, Lin Z (2000) Organometallics 19:2625CrossRefGoogle Scholar
  49. 49.
    He X, Hartwig JF (1996) Organometallics 15:400CrossRefGoogle Scholar
  50. 50.
    Rickard CEF, Roper WR, Williamson A, Wright LJ (2000) Organometallics 19:4344CrossRefGoogle Scholar
  51. 51.
    Dai C, Stringer G, Marder TB, Baker RT, Scott AJ, Clegg W, Norman NC (1996) Can J Chem 74:2026Google Scholar
  52. 52.
    Clegg W, Lawlor FJ, Marder TB, Nguyen P, Norman NC, Orpen AG, Quayle MJ, Rice CR, Robins EG, Scott AJ, Souza FES, Stringer G, Whittell GR (1998) J Chem Soc Dalton Trans 301Google Scholar
  53. 53.
    Dai C, Stringer G, Marder TB, Scott AJ, Clegg W, Norman NC (1997) Inorg Chem 36:272Google Scholar
  54. 54.
    Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF (2002) J Am Chem Soc 124:390CrossRefGoogle Scholar
  55. 55.
    Lu N, Norman NC, Orpen AG, Quayle MJ, Timms PL, Whittell GR (2000) Dalton Trans 4032Google Scholar
  56. 56.
    Rickard CEF, Roper WR, Williamson A, Wright LJ (1998) Organometallics 17:4869CrossRefGoogle Scholar
  57. 57.
    Rickard CEF, Roper WR, Williamson A, Wright LJ (1999) Angew Chem Int Ed Engl 38:1110CrossRefGoogle Scholar
  58. 58.
    Baker RT, Calabrese JC, Westcott SA, Nguyen P, Marder TB (1993) J Am Chem Soc 115:4367CrossRefGoogle Scholar
  59. 59.
    Marder TB, Norman NC, Rice CR, Robins EG (1997) Chem Commun 53Google Scholar
  60. 60.
    Clark GR, Irvine GJ, Roper WR, Wright LJ (2003) J Organomet Chem 680:81CrossRefGoogle Scholar
  61. 61.
    Dai C, Stringer G, Corrigan JF, Taylor NJ, Marder TB, Norman NC (1996) J Organomet Chem 513:273CrossRefGoogle Scholar
  62. 62.
    Lam KC, Lam WH, Lin Z, Marder TB, Norman NC (2004) Inorg Chem 43:2541CrossRefGoogle Scholar
  63. 63.
    Rossi AR, Hoffmann R (1975) Inorg Chem 14:365CrossRefGoogle Scholar
  64. 64.
    Takahashi K, Ishiyama T, Miyaura N (2000) Chem Lett 982Google Scholar
  65. 65.
    Takahashi K, Ishiyama T, Miyaura N (2001) J Organomet Chem 625:47CrossRefGoogle Scholar
  66. 66.
    Laitar DS, Müller P, Sadighi JP (2005) J Am Chem Soc 127:17196CrossRefGoogle Scholar
  67. 67.
    Zhao HT, Lin Z, Marder TB (2006) J Am Chem Soc 128:15637CrossRefGoogle Scholar
  68. 68.
    Laitar DS, Tsui EY, Sadighi JP (2006) J Am Chem Soc 128:11036CrossRefGoogle Scholar
  69. 69.
    Zhao HT, Dang L, Marder TB, Lin Z (2008) J Am Chem Soc 130:5586CrossRefGoogle Scholar
  70. 70.
    Ito H, Yamanaka H, Tateiwa J, Hosomi A (2000) Tetrahedron Lett 41:6821CrossRefGoogle Scholar
  71. 71.
    Lillo V, Prieto A, Bonet A, Dıáz-Requejo MM, Ramıŕez J, Peŕez PJ, Fernańdez E (2009) Organometallics 28:659CrossRefGoogle Scholar
  72. 72.
    Ali HA, Goldberg I, Srebnik M (2010) Organometallics 20:3962Google Scholar
  73. 73.
    Mun S, Lee JE, Yun J (2006) Org Lett 8:4887CrossRefGoogle Scholar
  74. 74.
    Sim HS, Feng X, Yun J (2009) Chem Eur J 15:1939CrossRefGoogle Scholar
  75. 75.
    Dang L, Lin Z, Marder TB (2008) Organometallics 27:4443CrossRefGoogle Scholar
  76. 76.
    Dang L, Zhao HT, Lin Z, Marder TB (2007) Organometallics 26:2824CrossRefGoogle Scholar
  77. 77.
    Laitar DS, Sadighi JP (2006) Organometallics 25:2405CrossRefGoogle Scholar
  78. 78.
    Segawa Y, Yamashita M, Nozaki K (2006) Science 314:113CrossRefGoogle Scholar
  79. 79.
    Kajiwara T, Terabayashi T, Yamashita M, Nozaki K (2008) Angew Chem Int Ed 47:6606CrossRefGoogle Scholar
  80. 80.
    Segawa Y, Suzuki Y, Yamashita M, Nozaki K (2008) J Am Chem Soc 130:16069CrossRefGoogle Scholar
  81. 81.
    Marder TB (2006) Science 314:64CrossRefGoogle Scholar
  82. 82.
    Braunschweig H (2007) Angew Chem Int Ed 46:1946CrossRefGoogle Scholar
  83. 83.
    Cheung MS, Mader TB, Lin Z (2011) Organometallics 30:3018CrossRefGoogle Scholar
  84. 84.
    Braunschweig H, Chiu CW, Radacki K, Kupfer T (2010) Angew Chem Int Ed 49:2041CrossRefGoogle Scholar
  85. 85.
    Yamashita M (2010) Angew Chem Int Ed 49:2474CrossRefGoogle Scholar
  86. 86.
    Monot J, Solovyev A, Bonin-Dubarle H, Derat E, Curran DP, Robert M, Fensterbank L, Malacria M, Lacote E (2010) Angew Chem Int Ed 49:9166CrossRefGoogle Scholar
  87. 87.
    Lin Z (2008) Struct Bonding (Berlin) 130:123CrossRefGoogle Scholar
  88. 88.
    Alcaraz G, Clot E, Helmstedt U, Vendier L, Sabo-Etienne S (2007) J Am Chem Soc 129:8704CrossRefGoogle Scholar
  89. 89.
    Alcaraz G, Grellier M, Sabo-Etienne S (2009) Acc Chem Res 42:1640CrossRefGoogle Scholar
  90. 90.
    Alcaraz G, Vendier L, Clot E, Sabo-Etienne S (2010) Angew Chem Int Ed 49:918CrossRefGoogle Scholar
  91. 91.
    Alcaraz G, Chaplin AB, Stevens CJ, Clot E, Vendier L, Weller S, Sabo-Etienne S (2010) Organometallics 29:5591CrossRefGoogle Scholar
  92. 92.
    Bénac-Lestrille G, Helmstedt U, Vendier L, Alcaraz G, Clot E, Sabo-Etienne S (2011) Inorg Chem 50:11039CrossRefGoogle Scholar
  93. 93.
    Gloaguen Y, Bénac-Lestrille G, Vendier L, Helmstedt U, Clot E, Alcaraz G, Sabo-Etienne S (2013) Organometallics 32:4868CrossRefGoogle Scholar
  94. 94.
    Gloaguen Y, Alcaraz G, Pécharman AF, Clot E, Vendier L, Sabo-Etienne S (2009) Angew Chem Int Ed 48:2964CrossRefGoogle Scholar
  95. 95.
    Gloaguen Y, Alcaraz G, Petit AS, Clot E, Coppel Y, Vendier L, Sabo-Etienne S (2011) J Am Chem Soc 133:17232CrossRefGoogle Scholar
  96. 96.
    Pandey KK (2009) Coord Chem Rev 253:37CrossRefGoogle Scholar
  97. 97.
    Pandey KK (2012) Dalton Trans 41:3278CrossRefGoogle Scholar
  98. 98.
    Braunschweig H, Radacki K, Seeler F, Whittell GR (2004) Organometallics 23:4178CrossRefGoogle Scholar
  99. 99.
    Braunschweig H, Radacki K, Seeler F, Whittell GR (2006) Organometallics 25:4605CrossRefGoogle Scholar
  100. 100.
    Braunschweig H, Radacki K, Rais D, Whittell GR (2005) Angew Chem Int Ed 44:1192CrossRefGoogle Scholar
  101. 101.
    Curtis D, Lesley, MJG, Norman NC, Orpen AG, Starbuck J (1999) J Chem Soc Dalton Trans 1687Google Scholar
  102. 102.
    Westcott SA, Marder TB, Baker RT, Harlow RL, Calabrese JC, Lam KC, Lin Z (2004) Polyhedron 23:2665CrossRefGoogle Scholar
  103. 103.
    Teltewskoi M, Panetier JA, Macgregor SA, Braun T (2010) Angew Chem Int Ed 49:3947CrossRefGoogle Scholar
  104. 104.
    Lawson YG, Lesley MJG, Marder TB, Norman NC, Rice CR (1997) Chem Commun 2051Google Scholar
  105. 105.
    Bell NJ, Cox AJ, Cameron NR, Evans JSO, Marder TB, Duin MA, Elsevier CJ, Baucherel X, Tulloch AAD, Tooze RP (2004) Chem Commun 1854Google Scholar
  106. 106.
    Liu B, Gao M, Dang L, Zhao HT, Marder TB, Lin Z (2012) Organometallics 31:3410CrossRefGoogle Scholar
  107. 107.
    Cid J, Carbó JJ, Fernández E (2012) Chem Eur J 18:12794CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  1. 1.Department of ChemistryThe Hong Kong University of Science and TechnologyKowloonHong Kong

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