Boron-Substituted Building Blocks in Diels-Alder and Other Cycloaddition Reactions

 

 Buy Article Permissions and Reprints All articles of this category

Abstract

Boron-containing building blocks are among the most prominent starting materials in several transformations based on their wide range of synthetic applications. Over the last decade various cycloaddition reactions were reported where boron-containing 1,3-dienes or boron-containing dienophiles were used. Combined with the broad follow-up chemistry, target-oriented as well as diversity-oriented syntheses could be established.

• 1 Introduction

• 2 Boron-Functionalised 1,3-Dienes

• 2.1 Boron in Position 1

• 2.2 Boron in Position 2

• 3 Boron-Functionalised Dienophiles

• 3.1 Alkenyl Boron Reagents

• 3.2 Alkynyl Boron Reagents

• 4 Boron Reagents in 1,3-Dipolar Cycloaddition

• 5 Miscellaneous

• 6 Outlook

References

• 1a Albrecht K. Kaufmann D. In Science of Synthesis (Houben-Weyl), Vol. 6   Thieme; New York: 2004.  p.697 
  CrossrefGoogle Scholar
• 1b Vaultier M. Alcaraz G. In Science of Synthesis (Houben-Weyl), Vol. 6   Thieme; New York: 2004.  p.721 
  CrossrefGoogle Scholar
• 1c Miyaura N. Top. Curr. Chem.  2002,  219:  11 
  CrossrefGoogle Scholar
• 1d Vaultier M. Lorvelec G. Plunian W. Paulus O. Bouju P. Mortier J. Royal Soc. Chem.  2000,  253:  464 
  CrossrefGoogle Scholar
• 1e Matteson DS. In Stereodirected Synthesis with Organoboranes   Springer; Berlin: 1995. 
  CrossrefGoogle Scholar
• 1f Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
  CrossrefGoogle Scholar
• 1g Matteson DS. Tetrahedron  1989,  45:  1859 
  CrossrefGoogle Scholar
• 2 Vaultier M. Truchet F. Carboni B. Hoffmann RW. Denne I. Tetrahedron Lett.  1987,  28:  4169 
  CrossrefGoogle Scholar
• 3 Mazal C. Vaultier M. Tetrahedron Lett.  1994,  35:  3089 
  CrossrefGoogle Scholar
• 4 Mikhailov BM. Cherkasova KL. Zh. Obshch. Khim.  1972,  42:  138 
  Google Scholar
• 5 Mikhailov BM. Cherkasova KL. Zh. Obshch. Khim.  1972,  42:  1744 
  Google Scholar
• 6 Renard P.-Y. Six Y. Lallemand J.-Y. Tetrahedron Lett.  1997,  38:  6589 
  CrossrefGoogle Scholar
• 7 Renard P.-Y. Lallemand J.-Y. Tetrahedron: Asymmetry  1996,  7:  2523 
  CrossrefGoogle Scholar
• 8 Garnier L. Plunian B. Mortier J. Vaultier M. Tetrahedron Lett.  1996,  37:  6699 
  CrossrefGoogle Scholar
• 9 Gao X. Hall DG. Tetrahedron Lett.  2003,  44:  2231 
  CrossrefGoogle Scholar
• 10 Wang X. J. Chem. Soc., Chem. Commun.  1991,  1515 
  CrossrefGoogle Scholar
• 11 Zhang A. Kan Y. Jiang B. Tetrahedron  2001,  57:  2305 
  CrossrefGoogle Scholar
• 12 Mortier J. Vaultier M. Plunian B. Toupet L. Heterocycles  1999,  50:  703 
  CrossrefGoogle Scholar
• 13 Renard P.-Y. Lallemand J.-Y. Bull. Soc. Chim. Fr.  1996,  133:  143 
  Google Scholar
• 14 Ohanessian G. Six Y. Lallemand J.-Y. Bull. Soc. Chim. Fr.  1996,  133:  1143 
  Google Scholar
• 15 Six Y. Lallemand J.-Y. Tetrahedron Lett.  1999,  40:  1295 
  CrossrefGoogle Scholar
• 16 Lallemand J.-Y. Six Y. Ricard L. Eur. J. Org. Chem.  2002,  503 
  CrossrefGoogle Scholar
• 17 Jehanno E. Vaultier M. Tetrahedron Lett.  1995,  36:  4439 
  CrossrefGoogle Scholar
• 18 Rasset-Deloge C. Martinez-Fresneda P. Vaultier M. Bull. Soc. Chim. Fr.  1992,  129:  285 
  Google Scholar
• 19 Deligny M. Carreaux F. Carboni B. Toupet L. Dujardin G. Chem. Commun.  2003,  276 
  CrossrefGoogle Scholar
• 20 Deligny M. Carreaux F. Toupet L. Carboni B. Adv. Synth. Catal.  2003,  345:  1215 
  CrossrefGoogle Scholar
• 21 Gao X. Hall DG. J. Am. Chem. Soc.  2003,  125:  9308 
  CrossrefPubMedGoogle Scholar
• 22 Gao X. Hall DG. J. Am. Chem. Soc.  2005,  127:  1628 
  CrossrefPubMedGoogle Scholar
• 23 Stierle DB. Stierle AA. Experientia  1992,  48:  1165 
  CrossrefGoogle Scholar
• 24 Tailor J. Hall DG. Org. Lett.  2000,  2:  3715 
  CrossrefGoogle Scholar
• 25 Touré BB. Hoveyda HR. Tailor J. Ulaczyk-Lesanko A. Hall DG. Chem.-Eur. J.  2003,  9:  466 
  Google Scholar
• 26 Touré BB. Hall DG. J. Org. Chem.  2004,  69:  8429 
  CrossrefGoogle Scholar
• 27 Touré BB. Hall DG. Angew. Chem. Int. Ed.  2004,  43:  2001 ; Angew. Chem. 2004, 116, 2035
  CrossrefGoogle Scholar
• 28 Guennouini N. Rasset-Deloge C. Carboni B. Vaultier M. Synlett  1992,  581 
  Article in Thieme ConnectGoogle Scholar
• 29 Kamabuchi A. Miyaura N. Suzuki A. Tetrahedron Lett.  1993,  34:  4827 
  CrossrefGoogle Scholar
• 30 Carreaux F. Possémé F. Carboni B. Arrieta A. Lecea B. Cossío FP. J. Org. Chem.  2002,  67:  9153 
  CrossrefGoogle Scholar
• 31 Shimizu M. Kurahashi T. Hiyama T. Synlett  2001,  1006 
  Article in Thieme ConnectGoogle Scholar
• 32 Kurahashi T. Hata T. Masai H. Kitagawa H. Shimizu M. Hiyama T. Tetrahedron  2002,  58:  6381 
  CrossrefGoogle Scholar
• 33 Waas JR. Sidduri A. Knochel P. Tetrahedron Lett.  1992,  33:  3717 
  CrossrefGoogle Scholar
• 34 Renaud J. Graf C.-D. Oberer L. Angew. Chem. Int. Ed.  2000,  39:  3101 ; Angew. Chem. 2000, 112, 3231
  CrossrefGoogle Scholar
• 35 Wrackmeyer B. Milius W. Bhatti MH. Ali S. J. Organomet. Chem.  2003,  665:  196 
  CrossrefGoogle Scholar
• 36 Kaufmann DE. Chem. Ber.  1987,  120:  901 
  CrossrefGoogle Scholar
• 37 Kaufmann DE. Schacht W. Chem. Ber.  1987,  120:  1331 
  CrossrefGoogle Scholar
• 38 Eisch JJ. Kotowicz BW. Eur. J. Inorg. Chem.  1998,  761 
  CrossrefGoogle Scholar
• 39 Matteson DS. Wasserbillig JO. J. Org. Chem.  1963,  28:  366 
  CrossrefGoogle Scholar
• 40 Matteson DS. Talbot ML. J. Am. Chem. Soc.  1967,  89:  1123 
  CrossrefGoogle Scholar
• 41 Woods WG. Bengelsdorf IS. J. Org. Chem.  1966,  31:  2769 
  CrossrefGoogle Scholar
• 42 Evans DA. Scott WL. Truesdale LK. Tetrahedron Lett.  1972,  2:  121 
  Google Scholar
• 43 Bonk JD. Avery MA. Tetrahedron: Asymmetry  1997,  8:  1149 
  CrossrefGoogle Scholar
• 44 Singleton DA. Martinez JP. J. Am. Chem. Soc.  1990,  112:  7423 
  CrossrefGoogle Scholar
• 45 Singleton DA. Martinez JP. Ndip GM. J. Org. Chem.  1992,  57:  5768 
  CrossrefGoogle Scholar
• 46 Singleton DA. Martinez JP. Watson JV. Ndip GM. Tetrahedron  1992,  48:  5831 
  CrossrefGoogle Scholar
• 47 Singleton DA. Martinez JP. Watson JV. Tetrahedron Lett.  1992,  33:  1017 
  CrossrefGoogle Scholar
• 48 Singleton DA. Martinez JP. Tetrahedron Lett.  1991,  32:  7365 
  CrossrefGoogle Scholar
• 49 Coindard G. Braun J. Bull. Soc. Chim. Fr.  1972,  817 
  Google Scholar
• 50 Singleton DA. Kim K. Martinez JP. Tetrahedron Lett.  1993,  34:  3071 
  CrossrefGoogle Scholar
• 51 Jego J.-M. Carboni B. Youssofi A. Vaultier M. Synlett  1993,  595 
  Article in Thieme ConnectGoogle Scholar
• 52 Noiret N. Youssofi A. Carboni B. Vaultier M. J. Chem. Soc., Chem. Commun.  1992,  1105 
  CrossrefGoogle Scholar
• 53 Lee Y.-K. Singleton DA. J. Org. Chem.  1997,  62:  2255 
  CrossrefPubMedGoogle Scholar
• 54 Singleton DA. J. Am. Chem. Soc.  1992,  114:  6563 
  CrossrefGoogle Scholar
• 55 Silva MA. Pellegrinet SC. Goodman JM. Arkivoc  2003,  x:  556 
  Google Scholar
• 56 Pellegrinet SC. Silva MA. Goodman JM. J. Am. Chem. Soc.  2001,  123:  8832 
  CrossrefPubMedGoogle Scholar
• 57 Pellegrinet SC. Silva MA. Goodman JM. J. Comput. Aided Mol. Des.  2004,  18:  209 
  CrossrefPubMedGoogle Scholar
• 58 Singleton DA. Redman AM. Tetrahedron Lett.  1994,  35:  509 
  CrossrefGoogle Scholar
• 59 Singleton DA. Leung S.-W. J. Organomet. Chem.  1997,  544:  157 
  CrossrefGoogle Scholar
• 60 Martinez-Fresneda P. Vaultier M. Tetrahedron Lett.  1989,  30:  2929 
  CrossrefGoogle Scholar
• 61 Rasset C. Vaultier M. Tetrahedron  1994,  50:  3397 
  CrossrefGoogle Scholar
• 62 Lorvelec G. Vaultier M. Tetrahedron Lett.  1998,  39:  5185 
  CrossrefGoogle Scholar
• 63 Singleton DA. Lee Y.-K. Tetrahedron Lett.  1995,  36:  3473 
  CrossrefGoogle Scholar
• 64 Batey RA. Lin D. Wong A. Hayhoe CLS. Tetrahedron Lett.  1997,  38:  3699 
  CrossrefGoogle Scholar
• 65 Batey RA. Thadani AN. Lough AJ. Chem. Commun.  1999,  475 
  CrossrefGoogle Scholar
• 66 Batey RA. Thadani AN. Lough AJ. J. Am. Chem. Soc.  1999,  121:  450 
  CrossrefGoogle Scholar
• 67 Narasaka K. Yamamoto I. Tetrahedron  1992,  48:  5743 
  CrossrefGoogle Scholar
• 68 Yamamoto I. Narasaka K. Bull. Chem. Soc. Jpn.  1994,  67:  3327 
  CrossrefGoogle Scholar
• 69 Blanchard C. Framery E. Vaultier M. Synthesis  1996,  45 
  Article in Thieme ConnectGoogle Scholar
• 70 Brown HC. Bhat NG. Srebnik M. Tetrahedron Lett.  1988,  29:  2631 
  CrossrefGoogle Scholar
• 71 For a review on the chemistry of alkynyl boronates, see: Negishi E. In Comprehensive Organometallic Chemistry   Vol. 7:  Wilkinson G. Stone FGA. Abel EW. Pergamon; Oxford: 1983.  p.337 
  Google Scholar
• 72 Matteson DS. Peacock K. J. Am. Chem. Soc.  1960,  82:  5759 
  Google Scholar
• 73 Matteson DS. J. Org. Chem.  1962,  27:  4293 
  CrossrefGoogle Scholar
• 74 Seitz G. Haenel F. Arch. Pharm.  1994,  327:  673 
  CrossrefGoogle Scholar
• 75 Leung S.-W. Singleton DA. J. Org. Chem.  1997,  62:  1955 
  CrossrefGoogle Scholar
• 76 Singleton DA. Leung S.-W. J. Org. Chem.  1992,  57:  4796 
  CrossrefGoogle Scholar
• 78 Silva MA. Pellegrinet SC. Goodman JM. J. Org. Chem.  2003,  68:  4059 
  CrossrefGoogle Scholar
• 79 Silva MA. Pellegrinet SC. Goodman JM. J. Org. Chem.  2002,  67:  8203 
  CrossrefGoogle Scholar
• 80 Silva MA. Goodman JM. Tetrahedron Lett.  2003,  44:  8233 
  CrossrefGoogle Scholar
• 81a Davies MW. Johnson CN. Harrity JPA. Chem. Commun.  1999,  2107 
  CrossrefGoogle Scholar
• 81b For a recent review, see: Dötz KH. Tomuschat P. Chem. Soc. Rev.  1999,  28:  187 
  CrossrefGoogle Scholar
• 82 Yamashita A. Tay A. Tetrahedron Lett.  1986,  27:  3471 
  CrossrefGoogle Scholar
• 83 Davies MW. Johnson CN. Harrity JPA. J. Org. Chem.  2001,  66:  3525 
  CrossrefGoogle Scholar
• 84a Vollhardt KPC. Eichberg MJ. In Strategies and Tactics in Organic Synthesis   Elsevier; London: 2004.  p.365 
  Google Scholar
• 84b Varela JA. Saa C. Chem. Rev.  2003,  103:  3787 
  Google Scholar
• 84c Saito S. Yamamoto Y. Chem. Rev.  2000,  100:  2901 
  Google Scholar
• 84d Vollhardt KPC. Lect. Heterocycl. Chem.  1987,  9:  59 
  Google Scholar
• 85 Gu Y. Pritzkow H. Siebert W. Eur. J. Inorg. Chem.  2001,  373 
  CrossrefGoogle Scholar
• 86 Goswami A. Maier C.-J. Pritzkow H. Siebert W. Eur. J. Org. Chem.  2004,  2635 
  CrossrefGoogle Scholar
• 87 Gandon V. Leca D. Aechtner T. Vollhardt KPC. Malacria M. Aubert C. Org. Lett.  2004,  6:  3405 
  CrossrefGoogle Scholar
• 88 Ester C. Maderna A. Pritzkow H. Siebert W. Eur. J. Inorg. Chem.  2000,  1177 
  CrossrefGoogle Scholar
• 89 Yamamoto Y. Ishii J.-i. Nishiyama H. Itoh K. J. Am. Chem. Soc.  2004,  126:  3712 
  CrossrefPubMedGoogle Scholar
• 90 Hilt G. Smolko KI. Angew. Chem.  2003,  115:  2901 ; Angew. Chem. Int. Ed. 2003, 42, 2795
  CrossrefGoogle Scholar
• 91 Hilt G. Hess W. Schmidt F. Eur. J. Org. Chem.  2005,  in press 
  Google Scholar
• 92 Hilt G. Lüers S. Smolko KI. Org. Lett.  2005,  7:  251 
  CrossrefGoogle Scholar
• 93 Jazouli M. Carboni B. Carrié R. Soufiaoui M. Toupet L. Heteroat. Chem.  1994,  5:  513 
  CrossrefGoogle Scholar
• 94 Wallace RH. Zong KK. Tetrahedron Lett.  1992,  33:  6941 
  CrossrefGoogle Scholar
• 95 Bast K. Christl M. Huisgen R. Mack W. Sustmann R. Chem. Ber.  1973,  106:  3258 
  CrossrefGoogle Scholar
• 96 Mukaiyama T. Hoshimo T. J. Am. Chem. Soc.  1960,  82:  5339 
  CrossrefGoogle Scholar
• 97 Jazouli M. Baba S. Carboni B. Carrié R. Soufiaoui M. J. Organomet. Chem.  1995,  498:  229 
  CrossrefGoogle Scholar
• 98 Wallace RH. Liu J. Tetrahedron Lett.  1994,  35:  7493 
  CrossrefGoogle Scholar
• 99 Grünanger P. Vita-Finzi P. In Isoxazoles   Vol. 49, Part 1:  Wiley; New York: 1991.  p.417 
  Google Scholar
• 100 Wallace RH. Liu J. Zong KK. Eddings A. Tetrahedron Lett.  1997,  38:  6791 
  CrossrefGoogle Scholar
• 101 Lui J. Eddings A. Wallace RH. Tetrahedron Lett.  1997,  38:  6795 
  CrossrefGoogle Scholar
• 102 Zhang A. Kan Y. Zhao G.-L. Jiang B. Tetrahedron  2000,  56:  965 
  CrossrefGoogle Scholar
• 103 Wallace RH. Zong KK. J. Organomet. Chem.  1999,  581:  87 
  CrossrefGoogle Scholar
• 104 Davies CD. Marsden SP. Stokes ESE. Tetrahedron Lett.  1998,  39:  8513 
  CrossrefGoogle Scholar
• 105 Davies CD. Marsden SP. Stokes ESE. Tetrahedron Lett.  2000,  41:  4229 
  CrossrefGoogle Scholar
• 106 Jiang B. Zhang A. Ying K. Chin. J. Chem.  1999,  17:  293 
  Google Scholar
• 107 Bianchi G. Cogoli A. Grünanger P. J. Organomet. Chem.  1966,  6:  598 
  CrossrefGoogle Scholar
• 108 Davies MW. Wybrow RAJ. Johnson CN. Harrity JPA. Chem. Commun.  2001,  1558 
  CrossrefGoogle Scholar
• 109 Moore JE. Goodenough KM. Spinks D. Harrity JPA. Synlett  2002,  2071 
  Article in Thieme ConnectGoogle Scholar
• 110 Carboni B. Ollivault M. Le Bouguenec F. Carrié R. Jazouli M. Tetrahedron Lett.  1997,  38:  6665 
  CrossrefGoogle Scholar
• 111 Belfaitah A. Isly M. Carboni B. Tetrahedron Lett.  2004,  45:  1969 
  CrossrefGoogle Scholar
• 112 Rastelli A. Gandolfi R. Sarzi-Amade M. Carboni B. J. Org. Chem.  2001,  66:  2449 
  CrossrefGoogle Scholar
• 113 Sáez J. Arnó M. Domingo LR. Tetrahedron  2003,  59:  9167 
  CrossrefGoogle Scholar
• 114 Micalizio GC. Schreiber SL. Angew. Chem. Int. Ed.  2002,  41:  152 ; Angew. Chem. 2002, 114, 160
  CrossrefGoogle Scholar
• 115 Micalizio GC. Schreiber SL. Angew. Chem. Int. Ed.  2002,  41:  3272 ; Angew. Chem. 2002, 114, 3406
  CrossrefGoogle Scholar
• 116 Pietruska J. Witt A. J. Chem. Soc., Perkin Trans. 1  2000,  4293 
  CrossrefGoogle Scholar
• 117 Markó IE. Kumamoto T. Giard T. Adv. Synth. Catal.  2002,  344:  1063 
  CrossrefGoogle Scholar
• 118 Markó IE. Giard T. Sumida S. Gies A.-E. Tetrahedron Lett.  2002,  43:  2317 
  CrossrefGoogle Scholar
• 119 Matteson DS. Schaumberg GD. J. Org. Chem.  1966,  31:  726 
  CrossrefGoogle Scholar
• 120 Bubnov YN. Nesmeyanova OA. Rudashevkaya TY. Mikhailov BM. Kazansky BA. Tetrahedron Lett.  1971,  24:  2153 
  Google Scholar
• 121 Little RD. Bode H. Stone KJ. Wallquist O. Dannecker R. J. Org. Chem.  1985,  50:  2401 
  CrossrefGoogle Scholar
• 122 Fontani P. Carboni B. Vaultier M. Carrié R. Tetrahedron Lett.  1989,  30:  4815 
  CrossrefGoogle Scholar
• 123 Fontani P. Carboni B. Vaultier M. Maas G. Synthesis  1991,  605 
  Article in Thieme ConnectGoogle Scholar
• 124 Imai T. Mineta H. Nishida S. J. Org. Chem.  1990,  55:  4986 
  CrossrefGoogle Scholar
• 125a Luithle JEA. Pietruszka J. Liebigs Ann./Recl.  1997,  2297 
  CrossrefPubMedGoogle Scholar
• 125b Pietruszka J. Widenmeyer M. Synlett  1997,  977 
  CrossrefPubMedGoogle Scholar
• 125c Luithle JEA. Pietruszka J. Witt A. Chem. Commun.  1998,  2651 
  CrossrefPubMedGoogle Scholar
• 125d Luithle JEA. Pietruszka J. J. Org. Chem.  1999,  64:  8287 
  CrossrefPubMedGoogle Scholar
• 125e Luithle JEA. Pietruszka J. J. Org. Chem.  2000,  65:  9194 
  CrossrefPubMedGoogle Scholar
• 126a Wang X.-Z. Deng M.-Z. J. Chem. Soc., Perkin Trans. 1  1996,  2663 
  CrossrefPubMedGoogle Scholar
• 126b Zhou S.-M. Yan Y.-L. Deng M.-Z. Synlett  1998,  198 
  CrossrefPubMedGoogle Scholar
• 126c Zhou S.-M. Deng M.-Z. Xia L.-J. Tang M.-H. Angew. Chem. Int. Ed.  1998,  37:  2845 ; Angew. Chem. 1998, 110, 3061
  CrossrefPubMedGoogle Scholar
• 127 Hildebrand JP. Marsden SP. Synlett  1996,  893 
  Article in Thieme ConnectGoogle Scholar
• 128 Charette AB. Pereira De Freitas-Gil R. Tetrahedron Lett.  1997,  38:  2809 
  CrossrefGoogle Scholar
• 129 Desurmont G. Klein R. Uhlenbrock S. Laloë E. Deloux L. Giolando DM. Kim YW. Pereira S. Srebnik M. Organometallics  1996,  15:  3323 
  CrossrefGoogle Scholar
• 130 Desurmont G. Dalton S. Giolando DM. Srebnik M. J. Org. Chem.  1997,  62:  8907 
  CrossrefGoogle Scholar
• 131 Hollis WG. Lappenbusch WC. Everberg KA. Woleben CM. Tetrahedron Lett.  1993,  34:  7517 
  CrossrefGoogle Scholar
• 132 Thormeier S. Carboni B. Kaufmann DE. J. Organomet. Chem.  2002,  657:  136 
  CrossrefGoogle Scholar

Early calculations on a RHF/3-21G level were consistent with the observed chemical behavior; compare ref. 76.