Issue 28, 2019

S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

Abstract

An unprecedented S8-catalyzed selective triple-cleavage of bromodifluoroacetamides is disclosed for the first time. Valuable 2-amido substituted benzimidazoles, benzoxazoles and benzothiazoles were obtained in good to excellent yields in a cascade protocol in this strategy. Mechanistic studies suggested that a C2 source was generated in situ by selective cleavage of three C–X bonds, including two inert C(sp3)–F bonds on bromodifluoroacetamides, while leaving C–C bonds intact. This strategy will undoubtedly further consummate the role of halo difluoro compounds and enrich both fluorine chemistry and pharmaceutical sciences.

Graphical abstract: S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

Supplementary files

Article information

Article type
Edge Article
Submitted
19 mar 2019
Accepted
31 maj 2019
First published
05 jun 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 6828-6833

S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles

S. Deng, H. Chen, X. Ma, Y. Zhou, K. Yang, Y. Lan and Q. Song, Chem. Sci., 2019, 10, 6828 DOI: 10.1039/C9SC01333D

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