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Computational Studies in Organometallic Chemistry pp 39–58Cite as

Reactivities and Electronic Properties of Boryl Ligands

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Part of the book series: Structure and Bonding ((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.

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References

  1. Baker RT, Ovenall DW, Calabrese JC, Westcott SA, Taylor NJ, Williams ID, Marder TB (1990) J Am Chem Soc 112:9399

    Article  CAS  Google Scholar 

  2. Knorr JR, Merola JS (1990) Organometallics 9:3008

    Article  CAS  Google Scholar 

  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 373

    Google Scholar 

  4. Wadepohl H (1997) Angew Chem Int Ed 36:2441

    Article  CAS  Google Scholar 

  5. Irvine GJ, Lesley MJG, Marder TB, Norman NC, Rice CR, Robins EG, Roper WR, Whittell GR, Wright LJ (1998) Chem Rev 98:2685

    Article  CAS  Google Scholar 

  6. Braunschweig H (1998) Angew Chem Int Ed 37:1786

    Article  CAS  Google Scholar 

  7. Smith MR (1999) Prog Inorg Chem 48:505

    Article  CAS  Google Scholar 

  8. Braunschweig H, Colling M (2001) Coord Chem Rev 223:1

    Article  CAS  Google Scholar 

  9. Coombs DL, Aldridge S (2004) Coord Chem Rev 248:535

    Article  Google Scholar 

  10. Braunschweig H, Whittell G (2005) Chem Eur J 11:6128

    Article  CAS  Google Scholar 

  11. Braunschweig H, Kollann C, Rais D (2006) Angew Chem Int Ed 45:5254

    Article  CAS  Google Scholar 

  12. Marder TB (2008) In: Fairlamb IJS, Lynam JM (eds) Specialist periodical reports: organometallic chemistry, vol 34. Royal Society of Chemistry, Cambridge, p 46

    Google Scholar 

  13. Kays DL, Aldridge S (2008) Struct Bonding (Berlin) 130:29

    Article  CAS  Google Scholar 

  14. Dang L, Lin ZY, Marder TB (2009) Chem Commun 3987

    Google Scholar 

  15. Mkhalid IA, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2010) Chem Rev 110:890

    Article  CAS  Google Scholar 

  16. Braunschweig H, Dewhurst RD, Schneider A (2010) Chem Rev 110:3924

    Article  CAS  Google Scholar 

  17. Braunschweig H, Dörfler R, Mies J, Oechsner A (2011) Chem Eur J 17:12101

    Article  CAS  Google Scholar 

  18. Cid J, Gulyás H, Carbó JJ, Fernández E (2012) Chem Soc Rev 41:3558

    Article  CAS  Google Scholar 

  19. Lillo V, Bonet A, Fernández E (2009) Dalton Trans 2899

    Google Scholar 

  20. Rablen PR, Hartwig JF, Nolan SP (1994) J Am Chem Soc 116:4121

    Article  CAS  Google Scholar 

  21. Sakaki S, Kai S, Sugimoto M (1999) Organometallics 18:4825

    Article  CAS  Google Scholar 

  22. Giju KT, Bickelhaupt FM, Frenking G (2000) Inorg Chem 39:4776

    Article  CAS  Google Scholar 

  23. Sivignon G, Fleurat-Lassard P, Onno JM, Volatron F (2002) Inorg Chem 41:6656

    Article  CAS  Google Scholar 

  24. Dickinson AA, Willock DJ, Calder RJ, Aldridge S (2002) Organometallics 21:1146

    Article  CAS  Google Scholar 

  25. Cundari TR, Zhao Y (2003) Inorg Chim Acta 345:70

    Article  CAS  Google Scholar 

  26. Lam WH, Shimada S, Batsanov AS, Lin Z, Marder TB, Cowan J, Howard JAK, Mason SA, McIntyre GJ (2003) Organometallics 22:4557

    Article  CAS  Google Scholar 

  27. Zhu J, Lin Z, Marder TB (2005) Inorg Chem 44:9384

    Article  CAS  Google Scholar 

  28. Braunschweig H, Brenner HP, Müller A, Radacki K, Rais D, Uttinger K (2007) Chem Eur J 13:7171

    Article  CAS  Google Scholar 

  29. Souza FES, Nguyen P, Marder TB, Scott AJ, Clegg W (2005) Inorg Chim Acta 358:1501

    Google Scholar 

  30. Westcott SA, Marder TB, Baker RT, Calabrese JC (1993) Can J Chem 71:930

    Article  CAS  Google Scholar 

  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 550:183

    Article  Google Scholar 

  32. Lesley G, Nguyen P, Taylor NJ, Marder TB, Scott AJ, Clegg W, Norman NC (1996) Organometallics 15:5137

    Article  CAS  Google Scholar 

  33. Braunschweig H, Leech R, Rais D, Radacki K, Uttinger K (2008) Organometallics 27:418

    Article  CAS  Google Scholar 

  34. Braunschweig H, Gruss K, Radacki K, Uttinger K (2008) Eur J Inorg Chem 1462

    Google Scholar 

  35. Braunschweig H, Fuβ M, Radacki K, Uttinger K (2009) Z Anorg Allg Chem 635:208

    Article  CAS  Google Scholar 

  36. Braunschweig H, Damme A, Kupfer T (2011) Angew Chem Int Ed 50:7179

    Article  CAS  Google Scholar 

  37. Bauer J, Braunschweig H, Kraft K, Radacki K (2011) Angew Chem Int Ed 50:10457

    Article  CAS  Google Scholar 

  38. Braunschweig H, Radacki K, Uttinger K (2008) Eur Chem J 14:7858

    Article  CAS  Google Scholar 

  39. Braunschweig H, Damme A, Kupfer T (2012) Eur Chem J 18:15927

    Article  CAS  Google Scholar 

  40. Arnold N, Braunschweig H, Brenner P, Jimenez-Halla JOC, Kupfer T, Radacki K (2012) Organometallics 31:1897

    Article  CAS  Google Scholar 

  41. Ishiyama T, Yamamoto M, Miyaura N (1996) Chem Lett 1117

    Google Scholar 

  42. Iverson CN, Smith MR III (1995) J Am Chem Soc 117:4403

    Article  CAS  Google Scholar 

  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 1431

    Google Scholar 

  44. Charmant JPH, Fan C, Norman NC, Pringle PG (2007) Dalton Trans 114

    Google Scholar 

  45. Braunschweig H, Brenner P, Dewhurst RD, Güthlein F, Jimenez-Halla JOC, Radacki K, Wolf J, Zöllner L (2012) Chem Eur J 18:8605

    Article  CAS  Google Scholar 

  46. Braunschweig H, Bertermann R, Brenner P, Burzler M, Dewhurst RD, Radacki K, Seeler F (2011) Chem Eur J 17:11828

    Article  CAS  Google Scholar 

  47. Hartwig JF, Muhoro CN, He X, Eisenstein O, Bosque R, Maseras F (1996) J Am Chem Soc 118:10936

    Article  CAS  Google Scholar 

  48. Lam WH, Lin Z (2000) Organometallics 19:2625

    Article  CAS  Google Scholar 

  49. He X, Hartwig JF (1996) Organometallics 15:400

    Article  CAS  Google Scholar 

  50. Rickard CEF, Roper WR, Williamson A, Wright LJ (2000) Organometallics 19:4344

    Article  CAS  Google Scholar 

  51. Dai C, Stringer G, Marder TB, Baker RT, Scott AJ, Clegg W, Norman NC (1996) Can J Chem 74:2026

    Google Scholar 

  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 301

    Google Scholar 

  53. Dai C, Stringer G, Marder TB, Scott AJ, Clegg W, Norman NC (1997) Inorg Chem 36:272

    Google Scholar 

  54. Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF (2002) J Am Chem Soc 124:390

    Article  CAS  Google Scholar 

  55. Lu N, Norman NC, Orpen AG, Quayle MJ, Timms PL, Whittell GR (2000) Dalton Trans 4032

    Google Scholar 

  56. Rickard CEF, Roper WR, Williamson A, Wright LJ (1998) Organometallics 17:4869

    Article  CAS  Google Scholar 

  57. Rickard CEF, Roper WR, Williamson A, Wright LJ (1999) Angew Chem Int Ed Engl 38:1110

    Article  CAS  Google Scholar 

  58. Baker RT, Calabrese JC, Westcott SA, Nguyen P, Marder TB (1993) J Am Chem Soc 115:4367

    Article  CAS  Google Scholar 

  59. Marder TB, Norman NC, Rice CR, Robins EG (1997) Chem Commun 53

    Google Scholar 

  60. Clark GR, Irvine GJ, Roper WR, Wright LJ (2003) J Organomet Chem 680:81

    Article  CAS  Google Scholar 

  61. Dai C, Stringer G, Corrigan JF, Taylor NJ, Marder TB, Norman NC (1996) J Organomet Chem 513:273

    Article  CAS  Google Scholar 

  62. Lam KC, Lam WH, Lin Z, Marder TB, Norman NC (2004) Inorg Chem 43:2541

    Article  CAS  Google Scholar 

  63. Rossi AR, Hoffmann R (1975) Inorg Chem 14:365

    Article  CAS  Google Scholar 

  64. Takahashi K, Ishiyama T, Miyaura N (2000) Chem Lett 982

    Google Scholar 

  65. Takahashi K, Ishiyama T, Miyaura N (2001) J Organomet Chem 625:47

    Article  CAS  Google Scholar 

  66. Laitar DS, Müller P, Sadighi JP (2005) J Am Chem Soc 127:17196

    Article  CAS  Google Scholar 

  67. Zhao HT, Lin Z, Marder TB (2006) J Am Chem Soc 128:15637

    Article  CAS  Google Scholar 

  68. Laitar DS, Tsui EY, Sadighi JP (2006) J Am Chem Soc 128:11036

    Article  CAS  Google Scholar 

  69. Zhao HT, Dang L, Marder TB, Lin Z (2008) J Am Chem Soc 130:5586

    Article  CAS  Google Scholar 

  70. Ito H, Yamanaka H, Tateiwa J, Hosomi A (2000) Tetrahedron Lett 41:6821

    Article  CAS  Google Scholar 

  71. Lillo V, Prieto A, Bonet A, Dıáz-Requejo MM, Ramıŕez J, Peŕez PJ, Fernańdez E (2009) Organometallics 28:659

    Article  CAS  Google Scholar 

  72. Ali HA, Goldberg I, Srebnik M (2010) Organometallics 20:3962

    Google Scholar 

  73. Mun S, Lee JE, Yun J (2006) Org Lett 8:4887

    Article  CAS  Google Scholar 

  74. Sim HS, Feng X, Yun J (2009) Chem Eur J 15:1939

    Article  CAS  Google Scholar 

  75. Dang L, Lin Z, Marder TB (2008) Organometallics 27:4443

    Article  CAS  Google Scholar 

  76. Dang L, Zhao HT, Lin Z, Marder TB (2007) Organometallics 26:2824

    Article  CAS  Google Scholar 

  77. Laitar DS, Sadighi JP (2006) Organometallics 25:2405

    Article  CAS  Google Scholar 

  78. Segawa Y, Yamashita M, Nozaki K (2006) Science 314:113

    Article  CAS  Google Scholar 

  79. Kajiwara T, Terabayashi T, Yamashita M, Nozaki K (2008) Angew Chem Int Ed 47:6606

    Article  CAS  Google Scholar 

  80. Segawa Y, Suzuki Y, Yamashita M, Nozaki K (2008) J Am Chem Soc 130:16069

    Article  CAS  Google Scholar 

  81. Marder TB (2006) Science 314:64

    Article  Google Scholar 

  82. Braunschweig H (2007) Angew Chem Int Ed 46:1946

    Article  CAS  Google Scholar 

  83. Cheung MS, Mader TB, Lin Z (2011) Organometallics 30:3018

    Article  CAS  Google Scholar 

  84. Braunschweig H, Chiu CW, Radacki K, Kupfer T (2010) Angew Chem Int Ed 49:2041

    Article  CAS  Google Scholar 

  85. Yamashita M (2010) Angew Chem Int Ed 49:2474

    Article  CAS  Google Scholar 

  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 49:9166

    Article  CAS  Google Scholar 

  87. Lin Z (2008) Struct Bonding (Berlin) 130:123

    Article  CAS  Google Scholar 

  88. Alcaraz G, Clot E, Helmstedt U, Vendier L, Sabo-Etienne S (2007) J Am Chem Soc 129:8704

    Article  CAS  Google Scholar 

  89. Alcaraz G, Grellier M, Sabo-Etienne S (2009) Acc Chem Res 42:1640

    Article  CAS  Google Scholar 

  90. Alcaraz G, Vendier L, Clot E, Sabo-Etienne S (2010) Angew Chem Int Ed 49:918

    Article  CAS  Google Scholar 

  91. Alcaraz G, Chaplin AB, Stevens CJ, Clot E, Vendier L, Weller S, Sabo-Etienne S (2010) Organometallics 29:5591

    Article  CAS  Google Scholar 

  92. Bénac-Lestrille G, Helmstedt U, Vendier L, Alcaraz G, Clot E, Sabo-Etienne S (2011) Inorg Chem 50:11039

    Article  Google Scholar 

  93. Gloaguen Y, Bénac-Lestrille G, Vendier L, Helmstedt U, Clot E, Alcaraz G, Sabo-Etienne S (2013) Organometallics 32:4868

    Article  CAS  Google Scholar 

  94. Gloaguen Y, Alcaraz G, Pécharman AF, Clot E, Vendier L, Sabo-Etienne S (2009) Angew Chem Int Ed 48:2964

    Article  CAS  Google Scholar 

  95. Gloaguen Y, Alcaraz G, Petit AS, Clot E, Coppel Y, Vendier L, Sabo-Etienne S (2011) J Am Chem Soc 133:17232

    Article  CAS  Google Scholar 

  96. Pandey KK (2009) Coord Chem Rev 253:37

    Article  CAS  Google Scholar 

  97. Pandey KK (2012) Dalton Trans 41:3278

    Article  CAS  Google Scholar 

  98. Braunschweig H, Radacki K, Seeler F, Whittell GR (2004) Organometallics 23:4178

    Article  CAS  Google Scholar 

  99. Braunschweig H, Radacki K, Seeler F, Whittell GR (2006) Organometallics 25:4605

    Article  CAS  Google Scholar 

  100. Braunschweig H, Radacki K, Rais D, Whittell GR (2005) Angew Chem Int Ed 44:1192

    Article  CAS  Google Scholar 

  101. Curtis D, Lesley, MJG, Norman NC, Orpen AG, Starbuck J (1999) J Chem Soc Dalton Trans 1687

    Google Scholar 

  102. Westcott SA, Marder TB, Baker RT, Harlow RL, Calabrese JC, Lam KC, Lin Z (2004) Polyhedron 23:2665

    Article  CAS  Google Scholar 

  103. Teltewskoi M, Panetier JA, Macgregor SA, Braun T (2010) Angew Chem Int Ed 49:3947

    Article  CAS  Google Scholar 

  104. Lawson YG, Lesley MJG, Marder TB, Norman NC, Rice CR (1997) Chem Commun 2051

    Google Scholar 

  105. Bell NJ, Cox AJ, Cameron NR, Evans JSO, Marder TB, Duin MA, Elsevier CJ, Baucherel X, Tulloch AAD, Tooze RP (2004) Chem Commun 1854

    Google Scholar 

  106. Liu B, Gao M, Dang L, Zhao HT, Marder TB, Lin Z (2012) Organometallics 31:3410

    Article  CAS  Google Scholar 

  107. Cid J, Carbó JJ, Fernández E (2012) Chem Eur J 18:12794

    Article  CAS  Google Scholar 

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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).

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  1. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong

    Zhenyang Lin

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  1. Zhenyang Lin
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Correspondence to Zhenyang Lin .

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Editors and Affiliations

  1. Institute of Chemical Sciences, Heriot-Watt Unversity, Edinburgh, United Kingdom

    Stuart A. Macgregor

  2. Institut Charles Gerhardt; UMR 5253-CNRS-UM-ENSCM, Université de Montpellier; Place E. Bataillon, Montpellier, France

    Odile Eisenstein

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Lin, Z. (2014). Reactivities and Electronic Properties of Boryl Ligands. In: Macgregor, S., Eisenstein, O. (eds) Computational Studies in Organometallic Chemistry. Structure and Bonding, vol 167. Springer, Cham. https://doi.org/10.1007/430_2014_148

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