title: Reaction of silyldihalomethyllithiums with nitriles: formation of alpha-keto acylsilanes via azirines and 1,3-rearrangement of silyl group from C to N.
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.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.
authors.forename: Kazunari
authors.initials: K
authors.lastname: Yagi
authors.forename: Takayuki
authors.initials: T
authors.lastname: Tsuritani
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Takami
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Shinokubo
authors.forename: Koichiro
authors.initials: K
authors.lastname: Oshima