Tin—Copper Transmetalation: Cross-Coupling of α-Heteroatom-Substituted Alkyltributylstannanes with Organohalides

Journal of the American Chemical Society

Volumn 117, Issue 22, 1995, Pages 5973-5982

  Falck, J R ^a   Bhatt, Rama K ^a   Ye, Jianhua ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000808892     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00127a010     Document Type: Article

References (28)

1. Reviews: (a) Mitchell, T. N. Synthesis 1992, 803—815.
2. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth: Boston, MA, 1987.
3. Behling, J. R.; Babiak, K. A.; Ng, J. S.; Campbell, A. L.; Moretti, R.; Koerner, M.; Lipshutz, B. H. J. Am. Chem. Soc. 1988, 110, 2641–2643.
4. Still, W. C.; Sreekumar, C. J. Am. Chem. Soc. 1980, 102, 1201–1202.
5. Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1991, 56, 5491–5493.
6. McGarvey, G. J.; Kimura, M. J. Am. Chem. Soc. 1985, 50, 4655–4657.
7. Liebeskind, L. S.; Foster, B. S. J. Am. Chem. Soc. 1990, 112, 8612–8613. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359–5364.
8. Malm, J.; Bjork, P.; Gronowitz, S.; Hörnfeldt, A.-B. Tetrahedron Lett. 1994, 35, 3195—3196. Satoh, T.; Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1994, 13, 4431—4436. Saa, J. M.; Martorell, G. J. Org. Chem. 1993, 58, 1963–1966. Liebeskind, L. S.; Riesinger, S. W. Tetrahedron Lett. 1993, 58, 408–413. Gomez-Bengoa, E.; Echavarren, A. M. Tetrahedron Lett. 1991, 56, 3497–3501. Palmisano, G.; Santagostino, M. Tetrahedron 1993, 49, 2533—2542. Ichikawa, J.; Ikeura, C.; Minami, T. Synlett 1992, 739—740.
9. Piers, E.; Wong, T. J. Org. Chem. 1993, 58, 3609–3610.
10. Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1—5.
11. Also see: (b) Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438—7439.
12. Ye, J.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1993, 34, 8007—8010.
13. The participation of coordinating or chelating heteroatom substituents in organometallic additions and stabilization has ample precedent: Hanessian, S.; Thavonekham, B.; DeHoff, B. J. Org. Chem. 1989, 54, 5831 - 5833 and cited references. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307–1370.
14. Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905–5911.
15. N2' products are obtained using conventionally prepared organocopper reagents: Lipshutz, B. H.; Sengupta, S. Org. React. 1982, 41, 135–631.
16. Lemarie, M.; Pham, T.-N.; Metzner, P. Tetrahedron Lett. 1991, 32, 7411–7414.
17. Marshall, J. A.; Gung, W.-Y. Tetrahedron Lett. 1989, 30, 2183–2186.
18. Chan, P.C.-M.; Chong, J. M. J. Org. Chem. 1988, 53, 5586–5588.
19. Labadie, J. W.; Stille, J. K. J. Am. Chem. Soc. 1983, 105, 6129–6137.
20. Freshly purified organic halides should be used to minimize this rearrangement which is also catalyzed by Bronsted acids: Fichtner, M. W.; Haley, N. F. J. Org. Chem. 1981, 46, 3141–3143.
21. Ho, T.-L. Chem. Rev. 1975, 75, 1–20.
22. A copper-promoted Michael-type addition of alkenyltributylstannanes has been reported: Tanaka, H.; Kameyama, Y.; Sumida, S.-I.; Torii, S. Tetrahedron Lett. 1992, 33, 7029—7030.
23. Bhatt, R. K.; Chauhan, K.; Wheelan, P.; Murphy, R. C.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 5050–5056.
24. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543–2549.
25. Bhatt, R. K.; Ye, J.; Falck, J. R. Tetrahedron Lett. 1994, 35, 4081–4084.
26. Bachi, M. D.; Bosch, E.; Denenmark, D.; Girsh, D. J. Org. Chem. 1992, 57, 6803–6810.
27. Racherla, U. S.; Brown, H. C. J. Org. Chem., 1991, 56, 401–404.
28. Riediker, M.; Duthaler, R. F. Angew. Chem., Int. Ed. Engl. 1989, 28, 494–495.