Selective copper-catalyzed coupling reactions of (α-acetoxyhexyl)tricyclohexyltin

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6492-6493

  Linderman, Russell J ^a   Siedlecki, James M ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000563359     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961161h     Document Type: Article

References (26)

1. (a) Labadie, J. W.; Tueting, D.; Stille, J. K. J. Org. Chem. 1983, 48, 4634-4642.
2. (b) For a review, see: Mitchell, T. N. Synthesis 1992, 803-815.
3. For additional examples of Pd catalyzed nonselective transfer of an α-alkoxyalkyl group, see: (c) Kosugi, M.; Sumiya, T.; Ogata, T.; Sano, H.; Migita, T. Chem. Lett. 1984, 1225-1226. (d) Majeed, A. J.; Antonsen, O.; Benneche, T.; Undheim, K. Tetrahedron 1989, 45, 993-1006.
4. For additional examples of Pd catalyzed nonselective transfer of an α-alkoxyalkyl group, see: (c) Kosugi, M.; Sumiya, T.; Ogata, T.; Sano, H.; Migita, T. Chem. Lett. 1984, 1225-1226. (d) Majeed, A. J.; Antonsen, O.; Benneche, T.; Undheim, K. Tetrahedron 1989, 45, 993-1006.
5. Ferezou, J. P.; Julia, M.; Li, Y.; Liu, W.; Pancrazi, A. Synlett 1991, 53-56.
6. (a) Vedejs, E.; Haight, A. R.; Moss, W. O. J. Am. Chem. Soc. 1992, 114, 6556-6558.
7. (b) For an internally activated tin hydride reagent, see: Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050.
8. (a) Linderman, R. J.; Graves, D. M.; Kwochka, W. R.; Ghannam, A. F.; Anklekar, T. V. J. Am. Chem. Soc. 1990, 112, 7438-7439.
9. (b) Siedlecki, J. M. Unpublished results.
10. (a) Ye, J.; Bhatt, R. K.; Falck, J. R. J. Am. Chem. Soc. 1994, 116, 1-5.
11. (b) Ye, J.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1993, 34, 8007-8010.
12. (c) Falck, J. R.; Bhatt, R. K.; Ye, J. J. Am. Chem. Soc. 1995, 117, 5973-5982.
13. (a) Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905-5911.
14. (b) Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1998, 118, 2748-2749.
15. (c) Piers, E.; McEachern, E. J.; Burns, P. A. J. Org. Chem. 1995, 60, 2322-2323.
16. (d) Piers, E.; McEachern, E. J.; Romero, M. A. Tetrahedron Lett. 1996, 37, 1173-1176.
17. Some butyl transfer is reported for α-phthaloylalkyl stannanes, but is not indicated for α-acetoxy stannane reactions in ref 5a. An interesting observation that carrying out the coupling reaction under CO favors Bu transfer is indicated in a footnote; however, no dimeric products (vida infra) are reported.
18. (a) Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1991, 56, 5491-5493.
19. (b) Linderman, R. J.; Griedel, B. D. J. Org. Chem. 1990, 55, 5428-5430.
20. (c) Linderman, R. J.; Godfrey, A.; Home, K. Tetrahedron 1989, 45, 495-506 and references therein.
21. 3) and Cu (Cul, CuCl, CuBr) sources and solvents (THF) were also examined.
22. The yields of 2 and 3 are calculated based on 1a. The yield of 4 is based on benzoyl chloride. The molar ratios were determined from the molar quantities of the isolated products and are therefore independent of starting material amounts. These data clearly indicate that dimer formation and Bu transfer are significant in reactions of stannane 1a.
23. The presence of oxygen is well known to induce oxidative coupling of organocopper and -cuprate species. For a recent synthetic example, see: Lipshutz, B. H.; Siegmann, K.; Garcia, E.; Kayser, F. J. Am. Chem. Soc. 1993, 115, 9276-9282.
24. 3SnLi, see: Jousseaume, B.; Lahcini, M.; Rascle, M.-C. Organometallics 1995, 14, 685-689.
25. Phenylcyclohexyl ketone 8 and dimer 3 were prepared independently. GC analysis of crude coupling reaction mixtures did not detect 3 or 8 in reactions using 1b.
26. 3 derivatives typically revealed a >30 ppm upfleld shift for complexed (trigonal bipyramidal at Sn) relative to uncomplexed (tetrahedral at Sn) species.