Carbon Dioxide-Catalyzed Stereoselective Cyanation Reaction

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We report a Michael-type cyanation reaction of coumarins by using CO2 as a catalyst. The delivery of the nucleophilic cyanide was realized by catalytic amounts of CO2, which forms cyanoformate and bicarbonate in the presence of water. Under ambient conditions, CO2-catalyzed reactions afforded high chemo- and diastereoselectivity of beta-nitrile carbonyls, whereas only low reactivities were observed under argon or N-2. Computational and experimental data suggest the catalytic role of CO2, which functions as a Lewis acid, and a protecting group to mask the reactivity of the product, suppressing byproducts and polymerization. The utility of this convenient method was demonstrated by preparing biologically relevant heterocyclic compounds with ease.
Publisher
AMER CHEMICAL SOC
Issue Date
2019-05
Language
English
Article Type
Article
Citation

ACS CATALYSIS, v.9, no.7, pp.6006 - 6011

ISSN
2155-5435
DOI
10.1021/acscatal.9b01087
URI
http://hdl.handle.net/10203/263856
Appears in Collection
CH-Journal Papers(저널논문)
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