Radical-mediated alkenylation, alkynylation, methanimination, and cyanation of B-alkylcatecholboranes

Angewandte Chemie - International Edition

Volumn 45, Issue 35, 2006, Pages 5847-5849

  Schaffner, Arnaud Pierre ^a   Darmency, Vincent ^a   Renaud, Philippe ^a  

^a UNIVERSITY OF BERN   (Switzerland)

Author keywords

C C coupling; Hydroboration; Olefination; Radical reactions; Sulfones

Indexed keywords

ACYLATION; ADDITION REACTIONS; OLEFINS; REACTION KINETICS;

C-C COUPLING; HYDROBORATION; RADICAL REACTIONS; SULFONES;

BORON COMPOUNDS;

ALKENE; ALKYNE; BORANE DERIVATIVE; CYANIDE; FREE RADICAL;

ARTICLE; CHEMISTRY;

ALKENES; ALKYNES; BORANES; CYANIDES; FREE RADICALS;

EID: 33748542324     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601206     Document Type: Article

References (55)

1. H. C. Brown, Angew. Chem. 1980, 92, 675.
2. H. C. Brown, Boranes in Organic Chemistry, Cornell University Press, Ithaca, 1972.
3. H. C. Brown, G. W. Kramer, A. B. Levy, M. M. Midland, Organic Synthesis via Boranes, Wiley, New York, 1975.
4. H. C. Brown, Hydroboration, Benjamin-Cumming, Reading, 1980.
5. A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, London, 1988.
6. D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer, Berlin, 1995.
7. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
8. For reviews on organoboron compounds, see : N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Vol. 219, Springer, Berlin, 2002.
9. F. Bellina, R. Rossi, Synthesis 2004, 2419.
10. H. C. Brown, M. M. Midland, Angew. Chem. 1972, 84, 702;
11. Angew. Chem. Int. Ed. Engl. 1972, 11, 692.
12. B. Giese, Radicals in Organic Syntheses: Formation of Carbon-Carbon Bonds, Pergamon, Oxford, 1986.
13. C. Ollivier, P. Renaud, Chem. Rev. 2001, 101, 3415.
14. A.-P. Schaffner, P. Renaud, Eur. J. Org. Chem. 2004, 2291.
15. V. Darmency, P. Renaud in Topics in Current Chemistry, Vol. 263 (Ed.: A. Gansaeuer), Springer, Berlin, 2006, p. 71.
16. A.-P. Schaffner, P. Renaud, Angew. Chem. 2003, 115, 2762;
17. Angew. Chem. Int. Ed. 2003, 42, 2658.
18. A.-P. Schaffner, B. Becattini, C. Ollivier, V. Weber, P. Renaud, Synthesis 2003, 2740.
19. V. Darmency, E. M. Scanlan, A.-P. Schaffner, P. Renaud, Org. Synth. 2005, 83, 24.
20. V. Darmency, P. Renaud, Chimia 2005, 59, 109.
21. F. Bertrand, F. Le Guyader, L. Liguori, G. Ouvry, B. Quiclet-Sire, S. Seguin, S. Z. Zard, C. R. Acad. Sci. Ser. II C 2001, 4, 547.
22. G. A. Russell, P. Ngoviwatchai, H. I. Tashtoush, A. Pladalmau, R. K. Khanna, J. Am. Chem. Soc. 1988, 110, 3530.
23. G. A. Russell, P. Ngoviwatchai, J. Org. Chem. 1989, 54, 1836.
24. N. Ono, A. Kamimura, A. Kaji, J. Org. Chem. 1987, 52, 5111.
25. A. J. Clark, S. Rooke, T. J. Sparey, P. C. Taylor, Tetrahedron Lett. 1996, 37, 909.
26. Recently, the first example of the introducion of a trimethylsilylethynyl group was reported: S. Usugi, H. Yorimitsu, H. Shinokubo, K. Oshima, Bull. Chem. Soc. Jpn. 2002, 75, 2687.
27. K. Takami, S. I. Usugi, H. Yorimitsu, K. Oshima, Synthesis 2005, 824.
28. K. Takami, H. Yorimitsu, K. Oshima, Org. Lett. 2004, 6, 4555.
29. For a review on radical fragmentation processes, see: I. J. Rosenstein in Radicals in Organic Synthesis, Vol. 1 (Eds.: P. Renaud, M. P. Sibi), Wiley-VCH, Weinheim, 2001, p. 50.
30. J. Xiang, P. L. Fuchs, J. Am. Chem. Soc. 1996, 118, 11 986.
31. J. Xiang, W. Jiang, J. Gong, P. L. Fuchs, J. Am. Chem. Soc. 1997, 119, 4123.
32. F. Bertrand, B. Quiclet-Sire, S. Z. Zard, Angew. Chem. 1999, 111, 2135;
33. Angew. Chem. Int. Ed. 1999, 38, 1943.
34. D. Leca, L. Fensterbank, E. Lacôte, M. Malacria, Angew. Chem. 2004, 116, 4316;
35. Angew. Chem. Int. Ed. 2004, 43, 4220.
36. D. Leca, K. Song, M. Albert, M. G. Goncalves, L. Fensterbank, E. Lacôte, M. Malacria, Synthesis 2005, 1405.
37. B. Delouvrié, L. Fensterbank, E. Lacôte, M. Malacria, J. Am. Chem. Soc. 1999, 121, 11 395.
38. N. Miyamoto, D. Fukuoka, K. Utimoto, H. Nozaki, Bull. Soc. Chem. Jpn. 1974, 47, 503.
39. J.-T. Liu, Y.-J. Jang, Y.-K. Shih, S.-R. Hu, C.-M. Chu, C.-F. Yao, J. Org. Chem. 2001, 66, 6021.
40. C.-F. Yao, C.-M. Chu, J.-T. Liu, J. Org. Chem. 1998, 63, 719.
41. C. E. Garett, G. C. Fu, J. Org. Chem. 1996, 61, 3224.
42. R. F. W. Jackson, S. P. Standen, W. Clegg, A. McCamley, J. Chem. Soc. Perkin Trans. 1 1995, 141.
43. a) S. Kim, I. Y. Lee, J.-Y. Yoon, D. H. Oh, J. Am. Chem. Soc. 1996, 5138;
44. b) S. Kim, C. J. Lim, Bull. Korean Chem. Soc. 2003, 24, 1219.
45. G. A. Russell, P. Ngoviwatchai, Tetrahedron Lett. 1986, 27, 3479.
46. J. C. Gong, P. L. Fuchs, J. Am. Chem. Soc. 1996, 118, 4486.
47. Coupling with a reverse polarity of the reagents (Sonogashira and Kumada-Corriu reactions), involving electrophilic alkyl halides with alkynyl nucleophiles are known: M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 13 642;
48. L. M. Yang, L.-F. Huang, T.-Y. Luh, Org. Lett. 2004, 6, 1461.
49. A procedure for the preparation of acetylene derivatives from organoboranes through iodine-mediated rearrangement of ate complexes has been reported: H. C. Brown, V. K. Mahindroo, N. G. Bhat, B. Singaram, J. Org. Chem. 1991, 56, 1500.
50. For a review on acetylenic sulfones, see: T. G. Back, Tetrahedron 2001, 57, 5263.
51. 3Si-substituted reagent 21, followed by desilylation and by alkylation of the terminal acetylene derivative.
52. Radical-mediated decarboxylative cyanation using tosyl cyanide has been reported: D. H. R. Barton, J. C. Jaszberenyi, E. A. Theodorakis, Tetrahedron 1992, 48, 2613.
53. J.-M. Fang, M.-Y. Chen, Tetrahedron Lett. 1987, 28, 2853.
54. S. Kim, H.-J. Song, Synlett 2002, 2110.
55. B. Becattini, C. Ollivier, P. Renaud, Synlett 2003, 1485.