title: Copper(I) tert-butoxide-promoted 1,4 C sp 2-to-O silyl migration: generation of vinyl copper equivalents and their stereospecific cross-coupling with allylic, aryl, and vinylic halides.
abstract: Successive treatment of the (Z)-gamma-trimethylsilyl allylic alcohols with copper(I) tert-butoxide and allylic halides followed by the tetrabutylammonium fluoride-assisted hydrolysis produced the allylation products, 2,5-alkadien-1-ols, with complete retention of configuration. Similar treatment of the organometallic intermediates with aryl and vinylic halides in the presence of palladium(0) catalyst gave the corresponding cross-coupling products in good yields. The stereoselective preparation of the starting materials is also described.
authors.affiliation: Department of Applied Chemistry, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Taguchi
authors.forename: Kazushi
authors.initials: K
authors.lastname: Ghoroku
authors.forename: Makoto
authors.initials: M
authors.lastname: Tadaki
authors.forename: Akira
authors.initials: A
authors.lastname: Tsubouchi
authors.forename: Takeshi
authors.initials: T
authors.lastname: Takeda