Alkynylboron compounds in organic synthesis

Journal of Organometallic Chemistry

Volumn 721-722, Issue , 2012, Pages 3-16

  Jiao, Jiao ^a   Nishihara, Yasushi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Addition reactions; Alkynylboron compounds; Cross coupling; Cycloaddition reactions; Zirconium

Indexed keywords

ADDITION REACTIONS; BORON; CYCLOADDITION; ZIRCONIUM;

ALKYNYLBORON COMPOUNDS; BORON ATOM; BUILDING BLOCKES; CROSS-COUPLINGS; CYCLOADDITION REACTION; FACILE SYNTHESIS; ORGANIC REACTION; ORGANIC SYNTHESIS;

SYNTHESIS (CHEMICAL);

EID: 84869497309     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.05.027     Document Type: Review

References (92)

1. A. Suzuki, and Y. Yamamoto Chem. Lett. 40 2011 894 901
2. H.C. Brown, and M. Srebnik Organometallics 6 1987 629 631
3. H.C. Borwn, N.G. Bhat, and M. Srebnik Tetrahedron Lett. 29 1988 2631 2634
4. N. Miyaura Bull. Chem. Soc. Jpn. 81 2008 1535 1553
5. H.C. Brown, and J.A. Sinclair J. Organomet. Chem. 131 1977 163 169
6. M. Yamaguchi, T. Waseda, and I. Hirao Chem. Lett. 12 1983 35 36
7. D.A. Singleton, and S. Leung J. Org. Chem. 57 1992 4796 4797
8. J.A. Soderquist, K. Matos, A. Rane, and J. Ramos Tetrahedron Lett. 36 1995 2401 2402
9. J.A. Soderquist, A.M. Rane, K. Matos, and J. Ramos Tetrahedron Lett. 36 1995 6847 6850
10. S.W. Leung, and D.A. Singleton J. Org. Chem. 62 1997 1955 1960
11. D.A. Singleton, and S. Leung J. Organomet. Chem. 544 1997 157 161
12. G.W. Kabalka, M. Yao, and S. Borella Org. Lett. 8 2006 879 881
13. V.V. Bardin, N.Y. Adonin, and H.-J. Frohn J. Fluorine Chem. 128 2007 699 702
14. N. Metzle, H. Nöth, and M. Thomann Organometallics 12 1993 2423 2425
15. C. Blanchard, M. Vaultier, and J. Mortier Tetrahedron Lett. 38 1997 8863 8866
16. L. Iannazzo, K.P.C. Vollhardt, M. Malacria, C. Aubert, and V. Gandon Eur. J. Org. Chem. 2011 3283 3292
17. H.C. Brown, and T.E. Cole Organometallics 2 1983 1316 1319
18. J.R. Struble, S.J. Lee, and M.D. Burke Tetrahedron 66 2010 4710 4718
19. E.J. Corey, and K.A. Cimprich J. Am. Chem. Soc. 116 1994 3151 3152
20. H. Chen, and M. Deng J. Organomet. Chem. 603 2000 189 193
21. S. Darses, J.P. Genêt, J.L. Brayer, and J.P. Demoute Tetrahedron Lett. 38 1997 4393 4396
22. S. Darses, G. Michaud, and J.P. Genêt Tetrahedron Lett. 39 1998 5045 5048
23. S. Darses, G. Michaud, and J.P. Genêt Eur. J. Org. Chem. 1999 1875 1883
24. J.F. Vivat, H. Adams, and J.P.A. Harrity Org. Lett. 12 2010 160 163
25. N. Ishida, Y. Shimamoto, and M. Murakami Org. Lett. 11 2009 5434 5437
26. M.A. Silva, S.C. Pellegrinet, and J.M. Goodman J. Org. Chem. 67 2002 8203 8209
27. J.E. Moore, K.M. York, and J.P.A. Harrity Synlett 2005 860 862
28. P.M. Delaney, J.E. Moore, and J.P.A. Harrity Chem. Commun. 2006 3323 3325
29. M.D. Helm, A. Plant, and J.P.A. Harrity Synlett 2007 2885 2887
30. M.D. Helm, J.E. Moore, A. Plant, and J.P.A. Harrity Angew. Chem. Int. Ed. 44 2005 3889 3892
31. E. Gomez-Bengoa, M.D. Helm, A. Plant, and J.P.A. Harrity J. Am. Chem. Soc. 129 2007 2691 2699
32. J.E. Moore, K.M. Goodenough, D. Spinks, and J.P.A. Harrity Synlett 2002 2071 2073
33. P.M. Delaney, J. Huang, S.J.F. F Macdonald, and J.P.A. Harrity Org. Lett. 10 2008 781 783
34. P.M. Delane, D.L. Browne, H. Adams, A. Plant, and J.P.A. Harrity Tetrahedron 64 2008 866 873
35. D.L. Browne, J.F. Vivat, A. Plant, E. Gomez-Bengoa, and J.P.A. Harrity J. Am. Chem. Soc. 131 2009 7762 7769
36. K.H. Dotz Angew. Chem. Int. Ed. 14 1975 644 645
37. M.W. Davies, J.P.A. Harrity, and C.N. Johnson Chem. Comm. 1999 2107 2108
38. M.W. Davies, C.N. Johnson, and J.P.A. Harrity J. Org. Chem. 66 2001 3525 3532
39. G. Hilt, and K.I. Smolko Angew. Chem. Int. Ed. 42 2003 2795 2797
40. G. Hilt, S. Lüers, and F. Schmidt Synthesis 2004 634 638
41. G. Hilt, W. Hess, and F. Schmidt Eur. J. Org. Chem. 2005 2526 2533
42. Y. Yamamoto, J. Ishii, H. Nishiyama, and K. Itoh J. Am. Chem. Soc. 126 2004 3712 3713
43. Y. Yamamoto, J. Ishii, H. Nishiyama, and K. Itoh Tetrahedron 61 2005 11501 11510
44. Y. Yamamoto, K. Hattori, J. Ishii, and H. Nishiyama Tetrahedron 62 2006 4294 4305
45. L. Deloux, and M. Srebnik J. Org. Chem. 59 1994 6871 6873
46. G. Desurmont, R. Klein, S. Uhlenbrock, E. Laloe, L. Deloux, D.M. Giolando, Y. Kim, S. Pereira, and M. Srebnik Organometallics 15 1996 3323 3328
47. A.A.A. Quntar, and M. Srebnik Org. Lett. 6 2004 4243 4244
48. A.A.A. Quntar, A. Botvinik, A. Rubinstein, and M. Srebnik Chem. Commun. 2008 5589 5591
49. A. Botvinik, A.A.A. Quntar, A. Rubinsein, and M. Srebnik J. Organomet. Chem. 694 2009 3349 3352
50. Y. Nishihara, M. Miyasaka, M. Okamoto, H. Takahashi, E. Inoue, K. Tanemura, and K. Takagi J. Am. Chem. Soc. 129 2007 12634 12635
51. Y. Nishihara, Y. Okada, J. Jiao, M. Suetsugu, M.-T. Lan, M. Kinoshita, M. Iwasaki, and K. Takagi Angew. Chem. Int. Ed. 50 2011 8660 8664
52. C.H. Oh, and V.R. Reddy Tetrahedron Lett. 45 2004 8545 8548
53. Y. Nishihara, D. Saito, E. Inoue, Y. Okada, M. Miyazaki, and Y. Inoue Tetrahedron Lett. 51 2010 306 308
54. Y. Nishihara, M. Okamoto, Y. Inoue, M. Miyazaki, M. Miyasaka, and K. Takagi Tetrahedron Lett. 46 2005 8661 8664
55. M.W. Paixão, M. Weber, A.L. Braga, J.B. Azeredo, A.M. Deobald, and H.A. Stefani Tetrahedron Lett 49 2008 2366 2370
56. G.H. Torres, S. Choppin, and F. Colobert Eur. J. Org. Chem. 2006 1450 1454
57. G.W. Kabalka, Z. Wu, S.E. Trotman, and X. Gao Org. Lett. 2 2000 255 256
58. G.W. Kabalka, Z. Wu, and Y. Ju Org. Lett. 4 2002 1491 1493
59. G.W. Kabalka, M. Yao, S. Borella, and Z. Wu Org. Lett. 7 2005 2865 2867
60. G.W. Kabalka, M. Yao, S. Borella, and Z. Wu Chem. Commun. 2005 2492 2494
61. G.W. Kabalka, and A.R. Mereddy Organometallics 23 2004 4519 4521
62. M. Yao, M.S. Reddy, L. Yong, I. Walfish, D.W. Blevin, and G.W. Kabalka Org. Lett. 12 2010 700 703
63. G.W. Kabalka, and A.R. Mereddy Tetrahedron Lett. 45 2004 1417 1419
64. G.W. Kabalka, A.R. Mereddy, J.F. Green, and J. Label Compd. Radiopharm. 49 2006 11 15
65. F. Lhermitte, and B. Carboni Synlett 1996 377 379
66. H.A. Ali, A.A.A. Quntar, I. Goldberg, and M. Srebnik Organometallics 21 2002 4533 4539
67. H. Li, P.J. Carroll, and P.J. Walsh J. Am. Chem. Soc. 130 2008 3521 3531
68. M.M. Hussain, H.M. Li, N. Hussain, M. Ureña, P.J. Carroll, and P.J. Walsh J. Am. Chem. Soc. 131 2009 6516 6524
69. J.M. Chong, L. Shen, and N.J. Taylor J. Am. Chem. Soc. 122 2000 1822 1823
70. J. Renaud, C.-D. Graf, and L. Oberer Angew. Chem. Int. Ed. 39 2000 3101 3104
71. M. Kim, and D. Lee Org. Lett. 7 2005 1865 1868
72. G.A. Molander, and N.M. Ellis J. Org. Chem. 73 2008 6841 6844
73. S.J. Lee, T.M. Anderson, and M.D. Burke Angew. Chem. Int. Ed. 49 2010 8860 8863
74. A. Pelter, and R.A. Drake Tetrahedron Lett. 29 1988 4181 4184
75. N. Ishida, T. Miura, and M. Murakami Chem. Commun. 2007 4381 4383
76. N. Ishida, M. Narumi, and M. Murakami Org. Lett. 10 2008 1279 1281
77. N. Ishida, Y. Shimamoto, and M. Murakami Org. Lett. 12 2010 3179 3181
78. B.M. Trost, A.F. Indolese, T.J.J. Müller, and B. Treptow J. Am. Chem. Soc. 117 1995 615 623
79. B.M. Trost, and F.D. Toste Tetrahedron Lett. 40 1999 7739 7743
80. B.M. Trost, A.B. Pinkerton, F.D. Toste, and M. Sperrle J. Am. Chem. Soc. 123 2001 12504 12509
81. E.C. Hansen, and D. Lee J. Am. Chem. Soc. 127 2005 3252 3253
82. E.C. Hansen, and D. Lee J. Am. Chem. Soc. 128 2006 8142 8143
83. C.S. Poulsen, and T. Madsen Synthesis 2003 1 18
84. S.J. Connon, and S. Blechert Angew. Chem. Int. Ed. 42 2003 1900 1923
85. A.J. Giessert, and S.T. Diver Chem. Rev. 104 2004 1317 1382
86. A.K. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360 11370
87. C. Morrill, and R.H. Grubbs J. Org. Chem. 68 2003 6031 6034
88. C. Morrill, T.W. Funk, and R.H. Grubbs Tetrahedron Lett. 45 2004 7733 7736
89. M. Suginome, M. Shirakura, and A. Yamamoto J. Am. Chem. Soc. 128 2006 14438 14439
90. T.R. Wu, and J.M. Chong J. Am. Chem. Soc. 127 2005 3244 3245
91. S.C. Pellegrinet, and J.M. Goodman J. Am. Chem. Soc. 128 2006 3116 3117
92. S. Crotti, F. Bertolini, F. Macchia, and M. Pineschi Chem. Commun. 2008 3127 3129