Highly Regio- and Stereoselective Carbostannylation Reaction of Fluorine-Containing Internal Acetylenes with Allylstannanes

• Published in: Journal of organic chemistry Vol. 69; no. 6; pp. 2188 - 2190
• Main Authors: Konno, Tsutomu, Takehana, Tsuyoshi, Chae, Jungha, Ishihara, Takashi, Yamanaka, Hiroki
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 19-03-2004
• Subjects: Aliphatic compounds; Chemistry; Exact sciences and technology; Organic chemistry; Preparations and properties; Stereoselectivity; Stille coupling; Alkene; Acetylenic compound; Regioselectivity; Air; Fluorine Organic compounds; Chemical synthesis; Allylic compound; Ethylenic compound; Organic stannane; Chemical coupling
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo030272v

Carbostannylation of fluoroalkylated alkynes with various allylstannanes in the presence of AIBN was investigated. In the case of the allylstannane having an electron-withdrawing group at the β position, the reaction proceeded highly regio- and stereoselectively to give the corresponding allylstannylated products in high yields. Even in the absence of AIBN, the reaction took place smoothly in a highly regio- and stereoselective manner under an atmosphere of air. Thus-obtained vinylstannanes were subjected to the Migita−Kosugi−Stille coupling reaction conditions, affording the tetrasubstituted alkenes in excellent yields.