Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 359, Issue 8, Pages 1339-1350Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201601024
Keywords
acrylonitriles; arylacetonitriles; base-promoted addition; nucleophilic addition; terminal alkynes
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Funding
- National Program on Key Research Project [2016YFA0602900]
- National Natural Science Foundation of China [21572071, 21490572]
- Fundamental Research Funds for the Central Universities [2015zz038]
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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.
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