Regioselective synthesis and cross coupling reactions of 1,2-borostannyl-1-alkenes

作者: Sunaina Sharma , Allan C. Oehlschlager

DOI: 10.1016/S0040-4039(00)80069-6

关键词:

摘要: Abstract The copper (I) catalyzed addition of Bu3Sn⊝BOCH3⋑ Li⊕ to 1-alkynes yields lithium[2-tri- n -butylstannyl-(Z)-1-alkenyl]-1-borates which may be selectively coupled via organopalladium or organocuprate chemistry with a variety electrophiles, exclusively at the vinyl boron bond. Products opposite regiochemistry are obtained when BF3·Et2O is added initial reaction and solution refluxed.

参考文章(14)
Eiichi Negishi, Tamotsu Takahashi, Shigeru Baba, David E. Van Horn, Nobuhisa Okukado, Palladium- or nickel-catalyzed reactions of alkenylmetals with unsaturated organic halides as a selective route to arylated alkenes and conjugated dienes: scope, limitations, and mechanism Journal of the American Chemical Society. ,vol. 109, pp. 2393- 2401 ,(1987) , 10.1021/JA00242A024
J. K. Stille, Palladium catalyzed coupling of organotin reagents with organic electrophiles Pure and Applied Chemistry. ,vol. 57, pp. 1771- 1780 ,(1985) , 10.1351/PAC198557121771
Kai Hsuan Chu, Kung K. Wang, Regio- and stereoselective synthesis of trisubstituted vinylstannanes Journal of Organic Chemistry. ,vol. 51, pp. 767- 768 ,(1986) , 10.1021/JO00355A043
Herbert C. Brown, N. G. Bhat, Shyamala. Rajagopalan, Stereospecific synthesis of the B-(Z)-1-alkenyl-9-borabicyclo[3.3.1]nonanes not available via hydroboration Organometallics. ,vol. 5, pp. 816- 818 ,(1986) , 10.1021/OM00135A036
W. Clark Still, Stannylation/destannylation. New syntheses of carbonyl compounds via organotin intermediates Journal of the American Chemical Society. ,vol. 99, pp. 4836- 4838 ,(1977) , 10.1021/JA00456A057
Kyoko Nozaki, Kuni Wakamatsu, Tsuyoshi Nonaka, Werner Tűckmantel, Koichiro Oshima, Kiitiro Utimoto, Transition-metal catalyzed regioselective addition of PhMe2SiBEt3Li and Bu3SnBEt3Li to acetylenic compounds in the presence of methanol Tetrahedron Letters. ,vol. 27, pp. 2007- 2010 ,(1986) , 10.1016/S0040-4039(00)84434-2