Carbon Dioxide-Mediated Catalytic Rearrangement of Propargyl Alcohols into α,β-Unsaturated Ketones

2007/10/01 by Yudai Sugawara, Wataru Yamada, Shunsuke Yoshida +2 · 1 citation
Chemical Engineering · Chemistry · #Carbon dioxide utilization in catalysis #Catalytic Alkyne Reactions #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja074350y

openalex publication_date 2007/10/01 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/26

Abstract

In the presence of a catalytic amount of a silver salt with DBU under a CO 2 atmosphere, various tertiary and secondary propargyl alcohols were efficiently converted into the corresponding α,β-unsaturated carbonyl compounds in high yield. An isotopic experiment using C 18 O 2 revealed that carbon dioxide mediated the rearrangement via an intramolecular nucleophilic attack on the alkyne activated by the silver catalyst.

Cited by

• Meyer–Schuster rearrangement [wikipedia]

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