Premium
A Convenient Catalytic Procedure for the Addition of Trimethylsilyl Cyanide to Functionalised Ketones, Mediated by InBr 3 − Insight into the Reaction Mechanism
Author(s) -
Bandini Marco,
Cozzi Pier Giorgio,
Garelli Andrea,
Melchiorre Paolo,
UmaniRonchi Achille
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200210)2002:19<3243::aid-ejoc3243>3.0.co;2-e
Subject(s) - chemistry , trimethylsilyl cyanide , catalysis , silylation , anhydrous , trimethylsilyl , organic chemistry , hydrogen cyanide , cyanide , combinatorial chemistry
This paper describes a useful and practical methodology for the addition of trimethylsilyl cyanide (TMSCN) to a large variety of functionalised and unfunctionalised ketones in the presence of catalytic amounts of anhydrous InBr 3 . The optimum procedure involves low catalyst loading (1 mol %) and appears general in scope and applicability for aromatic and aliphatic ketones. The desired cyanohydrins were typically isolated as their O ‐silyl ethers in good to excellent chemical yields (up to 99%). Kinetic and spectroscopic studies suggest that a catalytically active dimeric indium species is involved in the reaction mechanism. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)