Issue 13, 2024

Catalytic oxidative cyclization of α-carbonyl-γ-alkynyl sulfoxonium ylides for stereospecific synthesis of (1Z,3Z)-1,3-bismethyleneisobenzofurans

Abstract

A new copper(II)-catalyzed annulation-enabled radical addition cascade of α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfonyl hydrazides in the presence of tert-butyl hydroperoxide (TBHP) is reported, enabling a completely regio- and stereoselective strategy to access (1Z,3Z)-1,3-bismethyleneisobenzofurans in moderate-to-good yields. The protocol features a good substrate scope and functional group tolerance and proceeds through regioselective 5-exo-dig oxo-cyclization followed by stereoselective radical addition reaction.

Graphical abstract: Catalytic oxidative cyclization of α-carbonyl-γ-alkynyl sulfoxonium ylides for stereospecific synthesis of (1Z,3Z)-1,3-bismethyleneisobenzofurans

Supplementary files

Article information

Article type
Research Article
Submitted
23 Apr 2024
Accepted
10 May 2024
First published
10 May 2024

Org. Chem. Front., 2024,11, 3531-3536

Catalytic oxidative cyclization of α-carbonyl-γ-alkynyl sulfoxonium ylides for stereospecific synthesis of (1Z,3Z)-1,3-bismethyleneisobenzofurans

P. Zhou, W. Yang, W. Hao and B. Jiang, Org. Chem. Front., 2024, 11, 3531 DOI: 10.1039/D4QO00735B

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