Issue 14, 2024

Aerobic bimetallic catalysis for oxy-alkynylation of allenes

Abstract

Here we report a conceptual protocol to construct 4-alkynyl furan-2(5H)-one derivatives efficiently through Rh(III)/Cu(I) co-catalyzed highly regioselective oxy-alkynylation of 2,3-allenoic acids with terminal alkynes under mild aerobic conditions with atom economy. A wide variety of functional groups including biologically active groups have been tolerated. The synthetic potentials have also been demonstrated and the total syntheses of natural product appenolide A and its (Z)-isomer have been achieved by applying this protocol as the key step efficiently. A mechanism has been proposed based on mechanistic studies.

Graphical abstract: Aerobic bimetallic catalysis for oxy-alkynylation of allenes

Supplementary files

Article information

Article type
Research Article
Submitted
10 Apr 2024
Accepted
17 May 2024
First published
29 May 2024

Org. Chem. Front., 2024,11, 3842-3848

Aerobic bimetallic catalysis for oxy-alkynylation of allenes

J. Fan, D. Zhang, Y. Shi, C. Fu and S. Ma, Org. Chem. Front., 2024, 11, 3842 DOI: 10.1039/D4QO00622D

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