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Alkylative Preparation of α ‐Silylalkylmagnesium from R 3 SiCHBr 2 Using a Magnesate Reagent
Author(s) -
Kondo Junichi,
Inoue Atsushi,
Shinokubo Hiroshi,
Oshima Koichiro
Publication year - 2001
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20010601)40:11<2085::aid-anie2085>3.0.co;2-k
Subject(s) - reagent , silylation , yield (engineering) , magnesium , alkyl , bromine , chemistry , catalysis , chloride , organic chemistry , materials science , metallurgy
Magnesium–bromine exchange to provide the 1‐bromo‐1‐silylmethylmagnesium species is mediated by treatment of dibromomethylsilane with an trialkylmagnesate reagent. The addition of a copper catalyst induces facile migration of an alkyl group to afford an α ‐silylalkylmagnesium compound, which furnishes α ‐silyl ketones in good yield upon treatment with acyl chloride (see scheme).