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Formation of β-cyano-ketones through cyanide-promoted ring-opening of cyclic organic carbonates
Literature Information
Publication Date
2021-06-14
DOI
10.1039/D1QO00770J
Impact Factor
5.281
Authors
Jixiang Ni, Àlex Cristòfol
View Original
Abstract
Here we disclose a method for the unexpected decarboxylative cyanide-assisted ring-opening reaction of a series of vinyl cyclic carbonates. At elevated temperature, the attack of a cyanide nucleophile at the methylenic carbon center of the organic carbonate is promoted which leads to the release of CO2 and MeCN and the intermediacy of a Michael acceptor that undergoes facile 1,4-addition affording a β-cyano ketone product. This chemistry features a rare ring-opening reaction that is not initiated at the typically more electrophilic carbonate carbonyl.
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Source Journal
Organic Chemistry Frontiers
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7.8
Self-citation Rate:
8.7%
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
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