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Silver(I)-Promoted Cascade Reaction of Propargylic Alcohols, Carbon Dioxide, and Vicinal Diols: Thermodynamically Favorable Route to Cyclic Carbonates.

ABSTRACT: A silver(I)-promoted cascade reaction was developed for the synthesis of cyclic carbonates from terminal propargylic alcohols, carbon dioxide, and vicinal diols. Compared with direct condensation of vicinal diols with CO2, this protocol provides a thermodynamically favorable route to cyclic carbonates and ?-hydroxyl ketones in excellent yields (up to 97%) without the additional dehydration step. Such a cascade procedure proceeds presumably through initial reaction of propargylic alcohol with CO2 and subsequent nucleophilic attack of vicinal alcohol on in situ-formed ?-alkylidene cyclic carbonate, resulting in successive generation of ?-alkylidene cyclic carbonate, unsymmetrical ?-oxoalkyl carbonate, cyclic carbonate, and ?-hydroxyl ketone.

SUBMITTER: Zhou ZH

PROVIDER: S-EPMC6641138 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Silver(I)-Promoted Cascade Reaction of Propargylic Alcohols, Carbon Dioxide, and Vicinal Diols: Thermodynamically Favorable Route to Cyclic Carbonates.

Zhou Zhi-Hua ZH Song Qing-Wen QW He Liang-Nian LN

ACS omega 20170131 1

A silver(I)-promoted cascade reaction was developed for the synthesis of cyclic carbonates from terminal propargylic alcohols, carbon dioxide, and vicinal diols. Compared with direct condensation of vicinal diols with CO<sub>2</sub>, this protocol provides a thermodynamically favorable route to cyclic carbonates and α-hydroxyl ketones in excellent yields (up to 97%) without the additional dehydration step. Such a cascade procedure proceeds presumably through initial reaction of propargylic alcoh ...[more]

PMID: 31457234

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