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Gold Catalysis: Alkyl Migration in the Addition of Alcohols to Nitriles
Author(s) -
Ibrahim Nada,
Hashmi A. Stephen K.,
Rominger Frank
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000779
Subject(s) - chemistry , carbenium ion , catalysis , alcohol , alkyl , ether , ligand (biochemistry) , organic chemistry , medicinal chemistry , combinatorial chemistry , biochemistry , receptor
Benzhydroles and nitriles upon gold‐catalysed conversion deliver symmetrical ethers and/or N ‐substituted carboxylic amides. While with most phosphane ligands tested, the dominating product is always the ether, with the trimesitylene ligand the amides are the major products. The reaction conditions are much milder than those reported previously. Mechanistic control experiments with a chiral alcohol prove the intermediacy of carbenium ions, further studies with not readily ionisable alcohols indicate that for the benzhydroles the carbenium ions and gold(I)‐hydroxy complexes are intermediates.