Modular Synthesis of Tetrasubstituted Thioallenoates via the Tandem Wolff Rearrangement/C–S Bond Insertion Reaction of Alkynyl Diazoketones and N,S -Acetals

Organic Letters 2026

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Authors: Xuedi Zhao, Yuhao Ni, Zhihua Cai, Shengchao Yang, Lu Liu
DOI: 10.1021/acs.orglett.6c00595
Cited by: 4
References: 83

Abstract

Here, we present an approach for one-pot synthesis of tetrasubstituted thioallenoates via the addition of N,S -acetals to alkynyl ketenes generated in situ from alkynyl diazoalkyl ketones under photoirradiation. This reaction proceeds through a Wolff rearrangement/nucleophilic addition/1,5-migration cascade pathway, in which the alkynyl diazoalkyl ketones act as C4 synthons. This protocol is advantageous because of its mild conditions, short reaction time, broad substrate scope, and scale-up reaction.

Fields of Study & Subjects

Cyclopropane Reaction Mechanisms Catalytic C–H Functionalization Methods Sulfur-Based Synthesis Techniques

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
13
Pages
4084–4089
Publication date
19 March 2026
Language
EN