Metal-Free Intramolecular Carbocyanation of Activated Alkenes: Functionalized Nitriles Bearing β-Quaternary Carbon Centers

The CN shuffle: The described intramolecular alkenyl‐ and acylcyanation reaction of activated alkenes proceed by cleavage of a CN bond. This protocol provides access to functionalized acyclic nitriles with quaternary carbon centers under neutral and mild reaction conditions, demonstrates broad scop...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2013-08, Vol.52 (35), p.9296-9300
Main Authors: Chen, Jianming, Zou, Gongfeng, Liao, Weiwei
Format: Article
Language:English
Subjects:
Alkenes - chemistry
asymmetric synthesis
Carbon - chemistry
heterocycles
homogeneous catalysis
Molecular Structure
nitriles
Nitriles - chemical synthesis
Nitriles - chemistry
synthetic methods
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Summary:The CN shuffle: The described intramolecular alkenyl‐ and acylcyanation reaction of activated alkenes proceed by cleavage of a CN bond. This protocol provides access to functionalized acyclic nitriles with quaternary carbon centers under neutral and mild reaction conditions, demonstrates broad scope, and good functional‐group compatibility and versatility. Y=O or CHR4; R1,R4=electron‐withdrawing group; TBACN=tetrabutylammonium cyanide.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201304102