Nickel-Catalyzed Conjugate Addition of Alkynyl Groups to. α,β-Unsaturated Ketones

Jeffrey Schwartz, Denise B. Carr, Robert T. Hansen, Fabian M. Dayrit

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Abstract

The complex formed by reaction of Ni(acac)2 and DiBAH (1:1) catalyzes conjugate addition of dialkylaluminum acetylides to, ß enones; on hydrolysis, 3-alkynyl ketones are produced in high yield. Through this procedure conjugate addition of alkynyl groups to either S-cis or S-trans enones can be effected. This procedure is the first one which permits conjugate addition of terminal alkynyl units to ordinary S-trans enones. In cases where more than one stereochemical outcome is possible, conjugate addition of alkynyl units gives only one of these. Only 1,4-addition is observed and this only of the alkynyl unit. Complications arising from oxygen substitution in the alkynyl side chain are described.

Original languageEnglish (US)
Pages (from-to)3053-3061
Number of pages9
JournalJournal of Organic Chemistry
Volume45
Issue number15
DOIs
StatePublished - Jul 1980

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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