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Perfectly Green Organocatalysis: Quaternary Ammonium Base Triggered Cyanosilylation of Aldehydes
Author(s) -
Wen Yeqian,
Liang Mengwei,
Wang Yiming,
Ren Weimin,
Lü Xiaobing
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200598
Subject(s) - chemistry , trimethylsilyl cyanide , catalysis , organocatalysis , yield (engineering) , organic chemistry , ammonium , solvent , base (topology) , aqueous solution , enantioselective synthesis , mathematical analysis , materials science , mathematics , metallurgy
Quaternary ammonium bases, such as aqueous (CH 3 ) 4 NOH, were found to be an extraordinarily efficient catalyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide (TMSCN) to equivalent aldehydes could proceed smoothly with turnover frequency (TOF) up to 3 h −1 and in near 100% yield under solvent‐free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and α , β ‐unsaturated aldehydes. This process perfectly conforms to the features of green chemistry: no waste regarding side‐products and unconverted reactants, solvent‐free, excellent catalytic activity, and no requirement for separation.