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Updated: Jun 25, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Palladium-catalyzed sequential oxidative cyclization/coupling of 2-alkynylphenols and alkenes: a direct entry into
Claudio Martínez1, Rosana Alvarez, José M Aurrecoechea
1Departamento de Química Orgánica, Facultad de Química, Universidade de Vigo, Lagoas-Marcosende s/n, 36310 Vigo, Spain.
Abstract:
A new Pd-catalyzed tandem intramolecular oxypalladation/Heck-type coupling between 2-alkynylphenols and alkenes is reported, leading to 3-(1-alkenyl)benzofurans. Participating alkenes include those substituted with an electron-withdrawing group (ester, ketone, amide, nitrile, sulfone), as well as styrene. Remarkably, beta-substituted-alpha,beta-unsaturated carbonyl-type derivatives also participate effectively. The ready availability of substituted alkynylphenols, together with flexibility in the alkene choice, makes this simple strategy a versatile one for the synthesis of structurally diverse benzofuran derivatives.
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