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Updated: Apr 27, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Nucleopalladation-initiated oxyalkenylation of alkenes: a strategy to construct functionalized oxygenated
Liangbin Huang1, Qian Wang, Wanqing Wu
1School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou 510640, China.
Abstract:
A convenient and efficient approach to construct functionalized oxygen heterocycles, i.e., tetrahydrofurans, tetrahydropyrans, and γ-lactones, has been reported. This process successfully provides a route to construct derivatives of naturally occurring biologically active tetrahydrofurans, especially ones with spirocyclic structure. Highly regio- and stereoselective nucleopalladation of alkynes initiates the cross-coupling between alkynamides and alkenes to give the olefin oxyalkenylation products in good to excellent yields. The hydroxyl group in the olefins cooperates with the amide in alkynamides to promote the cyclization by suppressing the β-H elimination.
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