Reaction of Silyldihalomethyllithiums with Nitriles: Formation of α-Keto Acylsilanes via Azirines and 1,3-Rearrangement of Silyl Group from C to N
- 26 June 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (28) , 8618-8619
- https://doi.org/10.1021/ja047708o
Abstract
A synthesis of alpha-keto acylsilanes, where 2-bromo-2H-azirine participates as a key intermediate, is reported. The reaction of silyldibromomethyllithium with aryl nitriles provides alpha-keto acylsilanes in good yields. Interestingly, silyldichloromethyllithium induces aza-1,3-Brook rearrangement of the silyl group in th reaction with nitriles. The rearrangement enables a three-component coupling reaction in a one-pot operation.Keywords
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