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Chemoselective Silylzincation of Functionalized Terminal Alkynes Using Dianion-Type Zincate (SiBNOL-Zn-ate): Regiocontrolled Synthesis of Vinylsilanes
journal contribution
posted on 2004-09-15, 00:00 authored by Shinji Nakamura, Masanobu Uchiyama, Tomohiko OhwadaA regio- and chemoselective silylzincation reaction of various functionalized alkynes was developed using a newly designed dianion-type zincate. Silylzincation of terminal alkynes, followed by electrophilic trapping, proved to be a powerful tool for the one-pot, regiocontrolled generation of trisubstituted functionalized alkenes. The functionalized vinylzincate intermediate also undergoes copper- and palladium-catalyzed C−C bond-forming reactions in high yields and with high regio- and chemoselectivities.