Issue 20, 2024

Visible light-mediated gold-catalyzed alkynylative cyclization of allenoates with iodoalkynes for the synthesis of β-alkynyl-γ-butenolides

Abstract

A method for the tandem cyclization/alkynylation of allenoates with iodoalkynes via gold catalysis under light irradiation is described. This transformation features a broad substrate scope, good functional group tolerance, and compatibility with heterocyclic substrates. The reaction proceeds smoothly at room temperature by using cheap, readily available acriflavine (ACF) as a photocatalyst, and offers β-alkynyl-γ-butenolides derivatives in moderate to good yields. Initial mechanistic studies suggest that a vinylgold(I) complex acts as a key intermediate, which would undergo photosensitization from the ACF singlet excited state. The corresponding energy transfer would promote the oxidative addition of the iodoalkyne partner to deliver C(sp2)–C(sp) coupling products after reductive elimination.

Graphical abstract: Visible light-mediated gold-catalyzed alkynylative cyclization of allenoates with iodoalkynes for the synthesis of β-alkynyl-γ-butenolides

Supplementary files

Article information

Article type
Research Article
Submitted
23 Jun 2024
Accepted
31 Aug 2024
First published
07 Sep 2024

Org. Chem. Front., 2024,11, 5695-5702

Visible light-mediated gold-catalyzed alkynylative cyclization of allenoates with iodoalkynes for the synthesis of β-alkynyl-γ-butenolides

Y. He, Y. Zhong, M. B. Marion, J. C. H. Luna, W. Ma, Y. Hu, C. Ollivier, V. Mouriès-Mansuy, L. Fensterbank, F. Zhao, Z. Xia and B. Fan, Org. Chem. Front., 2024, 11, 5695 DOI: 10.1039/D4QO01153H

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