Perfectly Green Organocatalysis： Quaternary Ammonium Base Triggered Cyanosilylation of Aldehydes

Quaternary ammonium bases, such as aqueous （CH3）4NOH, were found to be an extraordinarily efficient cata-lyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide （TMSCN） to equivalent alde-hydes could proceed smoothly with turnover frequency （TOF） up to 3000000 h l and...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 30; no. 9; pp. 2109 - 2114
Main Author 温叶倩 梁梦伟 王忆铭 任伟民 吕小兵
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.09.2012
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Aldehydes
Ammonium
Chemistry
Chemistry, Multidisciplinary
cyanosilylation
Green chemistry
organocatalysis
Physical Sciences
quaternary ammonium base
Science & Technology
solvent-free
Solvents
三甲基硅基
不饱和醛
加成反应
季铵碱
有机催化剂
腈化
触发
醛化
ACTIVATION
quaternary ammonium base
SILICON
solvent-free
CATALYTIC CYANOSILYLATION
green chemistry
ENANTIOSELECTIVE CYANOSILYLATION
ATOM
organocatalysis
KETONES
cyanosilylation
ASYMMETRIC CYANOSILYLATION
CHEMISTRY
PENTACOORDINATE
TRIMETHYLSILYL CYANIDE
Online AccessGet full text
ISSN1001-604X
1614-7065
1614-7065
DOI10.1002/cjoc.201200598

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Summary:Quaternary ammonium bases, such as aqueous （CH3）4NOH, were found to be an extraordinarily efficient cata-lyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide （TMSCN） to equivalent alde-hydes could proceed smoothly with turnover frequency （TOF） up to 3000000 h l and in near 100% yield under solvent-free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and a,fl-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 separa- tion.
Bibliography:31-1547/O6
Wen, Yeqian Liang, Mengwei Wang, YimingRen, Weimin Lu, Xiaobing（State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, Liaoning 116024, China）
organocatalysis, green chemistry, cyanosilylation, quaternary ammonium base, solvent-free
Quaternary ammonium bases, such as aqueous （CH3）4NOH, were found to be an extraordinarily efficient cata-lyst for cyanosilylation of aldehydes. The addition reaction of trimethylsilyl cyanide （TMSCN） to equivalent alde-hydes could proceed smoothly with turnover frequency （TOF） up to 3000000 h l and in near 100% yield under solvent-free conditions. These organic catalysts also tolerated various aldehydes including aromatic, aliphatic and a,fl-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 separa- tion.
the National Natural Science Foundation of China (NSFC) - No. U1162101
ark:/67375/WNG-SWZDSXPQ-V
istex:31BDA90FACDBD81D9A4BDEB54FBADAE92F686904
National Basic Research Program of China (973) - No. 2009CB825300
ArticleID:CJOC201200598
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 14
ISSN:1001-604X
1614-7065
1614-7065
DOI:10.1002/cjoc.201200598