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Base‐Promoted Addition of Arylacetonitriles to Terminal Alkynes: Regio‐ and Stereoselective Access to Disubstituted Acrylonitriles
Author(s) -
Qi Chaorong,
Peng Youbin,
Ouyang Lu,
Ren Yanwei,
Jiang Huanfeng
Publication year - 2017
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.201601024
Subject(s) - chemistry , stereoselectivity , alkyne , substrate (aquarium) , nucleophilic addition , combinatorial chemistry , nucleophile , base (topology) , regioselectivity , nitrile , stereochemistry , organic chemistry , catalysis , mathematical analysis , oceanography , mathematics , geology
A base‐promoted nucleophilic addition of arylacetonitriles to terminal alkynes has been described for the first time, providing a simple and straightforward protocol for the synthesis of a range of structurally diverse ( Z )‐2,3‐disubstituted acrylonitriles in moderate to excellent yields. Of particular note, the transition metal‐free carbon‐carbon double bond forming reaction is regio‐ and stereoselective under mild conditions. A variety of functional groups can be tolerated on both the arylacetonitrile substrate and the alkyne coupling partner. Moreover, the reaction is easily scalable and the products thus obtained can serve as versatile intermediates for the synthesis of a series of useful substances.