A sequential highly stereoselective hydroboration and Suzuki–Miyaura cross-coupling reaction of fluoroalkylated internal acetylenes: a practical one-pot synthesis of fluoroalkylated trisubstituted alkenes

Literature Information

Publication Date 2004-02-12
DOI 10.1039/B316065C
Impact Factor 6.222
Authors

Tsutomu Konno, Jungha Chae, Tomoo Tanaka, Takashi Ishihara, Hiroki Yamanaka


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Abstract

The one-pot synthesis of trisubstituted alkenes starting from fluoroalkylated internal alkynes was investigated. Hydroboration of the alkynes proceeded in a highly regio- and stereoselective manner to give the corresponding vinylboranes in excellent yields. Without isolation, treatment of the vinylboranes with various aryl halides under the Suzuki–Miyaura cross-coupling conditions gave the fluoroalkylated trisubstituted alkenes in high yields with complete retention of the olefinic geometry.

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