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

Gerhard Hilt; Patrick Bolze

doi:10.1055/s-2005-872084

REVIEW

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

Gerhard Hilt*, Patrick Bolze
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35043 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: Hilt@chemie.uni-marburg.de;

Abstract

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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

Key words

boron - cycloaddition - cyclotrimerisation - Diels-Alder reaction - 1,3-dipole

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References

1a Albrecht K. Kaufmann D. In Science of Synthesis (Houben-Weyl), Vol. 6 Thieme; New York: 2004. p.697

1b Vaultier M. Alcaraz G. In Science of Synthesis (Houben-Weyl), Vol. 6 Thieme; New York: 2004. p.721

1c Miyaura N. Top. Curr. Chem. 2002, 219: 11

1d Vaultier M. Lorvelec G. Plunian W. Paulus O. Bouju P. Mortier J. Royal Soc. Chem. 2000, 253: 464

1e Matteson DS. In Stereodirected Synthesis with Organoboranes Springer; Berlin: 1995.

1f Miyaura N. Suzuki A. Chem. Rev. 1995, 95: 2457

1g Matteson DS. Tetrahedron 1989, 45: 1859

2 Vaultier M. Truchet F. Carboni B. Hoffmann RW. Denne I. Tetrahedron Lett. 1987, 28: 4169

3 Mazal C. Vaultier M. Tetrahedron Lett. 1994, 35: 3089

4 Mikhailov BM. Cherkasova KL. Zh. Obshch. Khim. 1972, 42: 138

5 Mikhailov BM. Cherkasova KL. Zh. Obshch. Khim. 1972, 42: 1744

6 Renard P.-Y. Six Y. Lallemand J.-Y. Tetrahedron Lett. 1997, 38: 6589

7 Renard P.-Y. Lallemand J.-Y. Tetrahedron: Asymmetry 1996, 7: 2523

8 Garnier L. Plunian B. Mortier J. Vaultier M. Tetrahedron Lett. 1996, 37: 6699

9 Gao X. Hall DG. Tetrahedron Lett. 2003, 44: 2231

10 Wang X. J. Chem. Soc., Chem. Commun. 1991, 1515

11 Zhang A. Kan Y. Jiang B. Tetrahedron 2001, 57: 2305

12 Mortier J. Vaultier M. Plunian B. Toupet L. Heterocycles 1999, 50: 703

13 Renard P.-Y. Lallemand J.-Y. Bull. Soc. Chim. Fr. 1996, 133: 143

14 Ohanessian G. Six Y. Lallemand J.-Y. Bull. Soc. Chim. Fr. 1996, 133: 1143

15 Six Y. Lallemand J.-Y. Tetrahedron Lett. 1999, 40: 1295

16 Lallemand J.-Y. Six Y. Ricard L. Eur. J. Org. Chem. 2002, 503

17 Jehanno E. Vaultier M. Tetrahedron Lett. 1995, 36: 4439

18 Rasset-Deloge C. Martinez-Fresneda P. Vaultier M. Bull. Soc. Chim. Fr. 1992, 129: 285

19 Deligny M. Carreaux F. Carboni B. Toupet L. Dujardin G. Chem. Commun. 2003, 276

20 Deligny M. Carreaux F. Toupet L. Carboni B. Adv. Synth. Catal. 2003, 345: 1215

21 Gao X. Hall DG. J. Am. Chem. Soc. 2003, 125: 9308

22 Gao X. Hall DG. J. Am. Chem. Soc. 2005, 127: 1628

23 Stierle DB. Stierle AA. Experientia 1992, 48: 1165

24 Tailor J. Hall DG. Org. Lett. 2000, 2: 3715

25 Touré BB. Hoveyda HR. Tailor J. Ulaczyk-Lesanko A. Hall DG. Chem.-Eur. J. 2003, 9: 466

26 Touré BB. Hall DG. J. Org. Chem. 2004, 69: 8429

27 Touré BB. Hall DG. Angew. Chem. Int. Ed. 2004, 43: 2001 ; Angew. Chem. 2004, 116, 2035

28 Guennouini N. Rasset-Deloge C. Carboni B. Vaultier M. Synlett 1992, 581

29 Kamabuchi A. Miyaura N. Suzuki A. Tetrahedron Lett. 1993, 34: 4827

30 Carreaux F. Possémé F. Carboni B. Arrieta A. Lecea B. Cossío FP. J. Org. Chem. 2002, 67: 9153

31 Shimizu M. Kurahashi T. Hiyama T. Synlett 2001, 1006

32 Kurahashi T. Hata T. Masai H. Kitagawa H. Shimizu M. Hiyama T. Tetrahedron 2002, 58: 6381

33 Waas JR. Sidduri A. Knochel P. Tetrahedron Lett. 1992, 33: 3717

34 Renaud J. Graf C.-D. Oberer L. Angew. Chem. Int. Ed. 2000, 39: 3101 ; Angew. Chem. 2000, 112, 3231

35 Wrackmeyer B. Milius W. Bhatti MH. Ali S. J. Organomet. Chem. 2003, 665: 196

36 Kaufmann DE. Chem. Ber. 1987, 120: 901

37 Kaufmann DE. Schacht W. Chem. Ber. 1987, 120: 1331

38 Eisch JJ. Kotowicz BW. Eur. J. Inorg. Chem. 1998, 761

39 Matteson DS. Wasserbillig JO. J. Org. Chem. 1963, 28: 366

40 Matteson DS. Talbot ML. J. Am. Chem. Soc. 1967, 89: 1123

41 Woods WG. Bengelsdorf IS. J. Org. Chem. 1966, 31: 2769

42 Evans DA. Scott WL. Truesdale LK. Tetrahedron Lett. 1972, 2: 121

43 Bonk JD. Avery MA. Tetrahedron: Asymmetry 1997, 8: 1149

44 Singleton DA. Martinez JP. J. Am. Chem. Soc. 1990, 112: 7423

45 Singleton DA. Martinez JP. Ndip GM. J. Org. Chem. 1992, 57: 5768

46 Singleton DA. Martinez JP. Watson JV. Ndip GM. Tetrahedron 1992, 48: 5831

47 Singleton DA. Martinez JP. Watson JV. Tetrahedron Lett. 1992, 33: 1017

48 Singleton DA. Martinez JP. Tetrahedron Lett. 1991, 32: 7365

49 Coindard G. Braun J. Bull. Soc. Chim. Fr. 1972, 817

50 Singleton DA. Kim K. Martinez JP. Tetrahedron Lett. 1993, 34: 3071

51 Jego J.-M. Carboni B. Youssofi A. Vaultier M. Synlett 1993, 595

52 Noiret N. Youssofi A. Carboni B. Vaultier M. J. Chem. Soc., Chem. Commun. 1992, 1105

53 Lee Y.-K. Singleton DA. J. Org. Chem. 1997, 62: 2255

54 Singleton DA. J. Am. Chem. Soc. 1992, 114: 6563

55 Silva MA. Pellegrinet SC. Goodman JM. Arkivoc 2003, x: 556

56 Pellegrinet SC. Silva MA. Goodman JM. J. Am. Chem. Soc. 2001, 123: 8832

57 Pellegrinet SC. Silva MA. Goodman JM. J. Comput. Aided Mol. Des. 2004, 18: 209

58 Singleton DA. Redman AM. Tetrahedron Lett. 1994, 35: 509

59 Singleton DA. Leung S.-W. J. Organomet. Chem. 1997, 544: 157

60 Martinez-Fresneda P. Vaultier M. Tetrahedron Lett. 1989, 30: 2929

61 Rasset C. Vaultier M. Tetrahedron 1994, 50: 3397

62 Lorvelec G. Vaultier M. Tetrahedron Lett. 1998, 39: 5185

63 Singleton DA. Lee Y.-K. Tetrahedron Lett. 1995, 36: 3473

64 Batey RA. Lin D. Wong A. Hayhoe CLS. Tetrahedron Lett. 1997, 38: 3699

65 Batey RA. Thadani AN. Lough AJ. Chem. Commun. 1999, 475

66 Batey RA. Thadani AN. Lough AJ. J. Am. Chem. Soc. 1999, 121: 450

67 Narasaka K. Yamamoto I. Tetrahedron 1992, 48: 5743

68 Yamamoto I. Narasaka K. Bull. Chem. Soc. Jpn. 1994, 67: 3327

69 Blanchard C. Framery E. Vaultier M. Synthesis 1996, 45

70 Brown HC. Bhat NG. Srebnik M. Tetrahedron Lett. 1988, 29: 2631

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

72 Matteson DS. Peacock K. J. Am. Chem. Soc. 1960, 82: 5759

73 Matteson DS. J. Org. Chem. 1962, 27: 4293

74 Seitz G. Haenel F. Arch. Pharm. 1994, 327: 673

75 Leung S.-W. Singleton DA. J. Org. Chem. 1997, 62: 1955

76 Singleton DA. Leung S.-W. J. Org. Chem. 1992, 57: 4796

77

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

78 Silva MA. Pellegrinet SC. Goodman JM. J. Org. Chem. 2003, 68: 4059

79 Silva MA. Pellegrinet SC. Goodman JM. J. Org. Chem. 2002, 67: 8203

80 Silva MA. Goodman JM. Tetrahedron Lett. 2003, 44: 8233

81a Davies MW. Johnson CN. Harrity JPA. Chem. Commun. 1999, 2107

81b For a recent review, see: Dötz KH. Tomuschat P. Chem. Soc. Rev. 1999, 28: 187

82 Yamashita A. Tay A. Tetrahedron Lett. 1986, 27: 3471

83 Davies MW. Johnson CN. Harrity JPA. J. Org. Chem. 2001, 66: 3525

84a Vollhardt KPC. Eichberg MJ. In Strategies and Tactics in Organic Synthesis Elsevier; London: 2004. p.365

84b Varela JA. Saa C. Chem. Rev. 2003, 103: 3787

84c Saito S. Yamamoto Y. Chem. Rev. 2000, 100: 2901

84d Vollhardt KPC. Lect. Heterocycl. Chem. 1987, 9: 59

85 Gu Y. Pritzkow H. Siebert W. Eur. J. Inorg. Chem. 2001, 373

86 Goswami A. Maier C.-J. Pritzkow H. Siebert W. Eur. J. Org. Chem. 2004, 2635

87 Gandon V. Leca D. Aechtner T. Vollhardt KPC. Malacria M. Aubert C. Org. Lett. 2004, 6: 3405

88 Ester C. Maderna A. Pritzkow H. Siebert W. Eur. J. Inorg. Chem. 2000, 1177

89 Yamamoto Y. Ishii J.-i. Nishiyama H. Itoh K. J. Am. Chem. Soc. 2004, 126: 3712

90 Hilt G. Smolko KI. Angew. Chem. 2003, 115: 2901 ; Angew. Chem. Int. Ed. 2003, 42, 2795

91 Hilt G. Hess W. Schmidt F. Eur. J. Org. Chem. 2005, in press

92 Hilt G. Lüers S. Smolko KI. Org. Lett. 2005, 7: 251

93 Jazouli M. Carboni B. Carrié R. Soufiaoui M. Toupet L. Heteroat. Chem. 1994, 5: 513

94 Wallace RH. Zong KK. Tetrahedron Lett. 1992, 33: 6941

95 Bast K. Christl M. Huisgen R. Mack W. Sustmann R. Chem. Ber. 1973, 106: 3258

96 Mukaiyama T. Hoshimo T. J. Am. Chem. Soc. 1960, 82: 5339

97 Jazouli M. Baba S. Carboni B. Carrié R. Soufiaoui M. J. Organomet. Chem. 1995, 498: 229

98 Wallace RH. Liu J. Tetrahedron Lett. 1994, 35: 7493

99 Grünanger P. Vita-Finzi P. In Isoxazoles Vol. 49, Part 1: Wiley; New York: 1991. p.417

100 Wallace RH. Liu J. Zong KK. Eddings A. Tetrahedron Lett. 1997, 38: 6791

101 Lui J. Eddings A. Wallace RH. Tetrahedron Lett. 1997, 38: 6795

102 Zhang A. Kan Y. Zhao G.-L. Jiang B. Tetrahedron 2000, 56: 965

103 Wallace RH. Zong KK. J. Organomet. Chem. 1999, 581: 87

104 Davies CD. Marsden SP. Stokes ESE. Tetrahedron Lett. 1998, 39: 8513

105 Davies CD. Marsden SP. Stokes ESE. Tetrahedron Lett. 2000, 41: 4229

106 Jiang B. Zhang A. Ying K. Chin. J. Chem. 1999, 17: 293

107 Bianchi G. Cogoli A. Grünanger P. J. Organomet. Chem. 1966, 6: 598

108 Davies MW. Wybrow RAJ. Johnson CN. Harrity JPA. Chem. Commun. 2001, 1558

109 Moore JE. Goodenough KM. Spinks D. Harrity JPA. Synlett 2002, 2071

110 Carboni B. Ollivault M. Le Bouguenec F. Carrié R. Jazouli M. Tetrahedron Lett. 1997, 38: 6665

111 Belfaitah A. Isly M. Carboni B. Tetrahedron Lett. 2004, 45: 1969

112 Rastelli A. Gandolfi R. Sarzi-Amade M. Carboni B. J. Org. Chem. 2001, 66: 2449

113 Sáez J. Arnó M. Domingo LR. Tetrahedron 2003, 59: 9167

114 Micalizio GC. Schreiber SL. Angew. Chem. Int. Ed. 2002, 41: 152 ; Angew. Chem. 2002, 114, 160

115 Micalizio GC. Schreiber SL. Angew. Chem. Int. Ed. 2002, 41: 3272 ; Angew. Chem. 2002, 114, 3406

116 Pietruska J. Witt A. J. Chem. Soc., Perkin Trans. 1 2000, 4293

117 Markó IE. Kumamoto T. Giard T. Adv. Synth. Catal. 2002, 344: 1063

118 Markó IE. Giard T. Sumida S. Gies A.-E. Tetrahedron Lett. 2002, 43: 2317

119 Matteson DS. Schaumberg GD. J. Org. Chem. 1966, 31: 726

120 Bubnov YN. Nesmeyanova OA. Rudashevkaya TY. Mikhailov BM. Kazansky BA. Tetrahedron Lett. 1971, 24: 2153

121 Little RD. Bode H. Stone KJ. Wallquist O. Dannecker R. J. Org. Chem. 1985, 50: 2401

122 Fontani P. Carboni B. Vaultier M. Carrié R. Tetrahedron Lett. 1989, 30: 4815

123 Fontani P. Carboni B. Vaultier M. Maas G. Synthesis 1991, 605

124 Imai T. Mineta H. Nishida S. J. Org. Chem. 1990, 55: 4986

125a Luithle JEA. Pietruszka J. Liebigs Ann./Recl. 1997, 2297

125b Pietruszka J. Widenmeyer M. Synlett 1997, 977

125c Luithle JEA. Pietruszka J. Witt A. Chem. Commun. 1998, 2651

125d Luithle JEA. Pietruszka J. J. Org. Chem. 1999, 64: 8287

125e Luithle JEA. Pietruszka J. J. Org. Chem. 2000, 65: 9194

126a Wang X.-Z. Deng M.-Z. J. Chem. Soc., Perkin Trans. 1 1996, 2663

126b Zhou S.-M. Yan Y.-L. Deng M.-Z. Synlett 1998, 198

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

127 Hildebrand JP. Marsden SP. Synlett 1996, 893

128 Charette AB. Pereira De Freitas-Gil R. Tetrahedron Lett. 1997, 38: 2809

129 Desurmont G. Klein R. Uhlenbrock S. Laloë E. Deloux L. Giolando DM. Kim YW. Pereira S. Srebnik M. Organometallics 1996, 15: 3323

130 Desurmont G. Dalton S. Giolando DM. Srebnik M. J. Org. Chem. 1997, 62: 8907

131 Hollis WG. Lappenbusch WC. Everberg KA. Woleben CM. Tetrahedron Lett. 1993, 34: 7517

132 Thormeier S. Carboni B. Kaufmann DE. J. Organomet. Chem. 2002, 657: 136