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Nitrile Alkylations through Sulfinyl–Metal Exchange
Author(s) -
Nath Dinesh,
Fleming Fraser F.
Publication year - 2011
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/anie.201105630
Subject(s) - nitrile , electrophile , alkylation , acetonitrile , chemistry , metal , combinatorial chemistry , computer science , organic chemistry , catalysis
Triple alkylation : Phenylsulfinyl‐ and phenylthioacetonitrile can function as trianion equivalents of acetonitrile by sequential alkylation and sulfinyl–metal exchange (see scheme; m CPBA= meta ‐chloroperoxybenzoic acid). The metalated nitriles alkylate a range of electrophiles to obtain nitriles with quaternary centers. The sulfinyl–metal exchange proceeds under very mild conditions and has a high functional‐group tolerance.