Heavier Carbonyl Olefination: The Sila-Wittig Reaction

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...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 141; no. 42; pp. 16991 - 16996
Main Authors Reiter, Dominik, Frisch, Philipp, Szilvási, Tibor, Inoue, Shigeyoshi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.10.2019
Amer Chemical Soc
Subjects
alkenes
carbon
carbonyl compounds
Chemistry
Chemistry, Multidisciplinary
cycloaddition reactions
ketones
Lewis bases
Physical Sciences
Science & Technology
silicon
zwitterions
ADDUCTS
YLIDES
DERIVATIVES
SILICON
BONDS
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Summary: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.
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.9b09379