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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.

SUBMITTER: Deng S

PROVIDER: S-EPMC6657413 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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

Deng Shuilin S Chen Haohua H Ma Xingxing X Zhou Yao Y Yang Kai K Lan Yu Y Song Qiuling Q

Chemical science 20190605 28

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 ...[more]

PMID: 31391905

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