Heavier Carbonyl Olefination: The Sila-Wittig Reaction

Dominik Reiter, Philipp Frisch, Tibor Szilvási, Shigeyoshi Inoue

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

The Wittig reaction is one of the most versatile tools in the repertoire of organic chemists. Thus, a broad variety of carbonyl compounds can be converted to tailor-made alkenes with phosphorus ylides under mild conditions. However, no comparable reaction has been reported for silanones, the silicon congeners of ketones. Here, we demonstrate for the first time the successful application of the Wittig olefination to iminosilylsilanone 1. The selective formation of a series of silenes (R2Si═CR2) via the sila-Wittig reaction revealed an unprecedented approach to otherwise elusive compounds. In addition, the highly reactive and zwitterionic nature of 1 was also susceptible to nucleophilic attacks and cycloaddition reactions by and with the phosphorus ylides. Our results therefore make another important contribution to discovering the differences and similarities between carbon and silicon.

Original languageEnglish
Pages (from-to)16991-16996
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number42
DOIs
StatePublished - 23 Oct 2019

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