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

Chemical Science
Shuilin DengQiuling Song

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.

References

Apr 1, 2009·Chemical Reviews·Hideki Amii, Kenji Uneyama
Nov 1, 2013·Journal of the American Chemical Society·Mingyou HuJinbo Hu
Mar 30, 2016·The Journal of Organic Chemistry·Miaolin Ke, Qiuling Song
Sep 9, 2016·Angewandte Chemie·Ji-Wei GuXingang Zhang
Nov 17, 2017·Angewandte Chemie·Jiao YuJi-Chang Xiao
Jun 23, 2018·Chemical Communications : Chem Comm·Xingxing MaQiuling Song
Jul 11, 2018·Journal of the American Chemical Society·Minyan WangZhuangzhi Shi
Sep 5, 2018·Journal of the American Chemical Society·Sheng-Qing ZhuFeng-Ling Qing

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Citations

Jul 11, 2020·Organic & Biomolecular Chemistry·Loan T TranNam T S Phan
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Satenik MkrtchyanViktor O Iaroshenko
Aug 19, 2021·Nature Communications·Jianke SuQiuling Song
Nov 12, 2020·The Journal of Organic Chemistry·Shaoqun ZhuHong Hou
Dec 7, 2021·Acta Crystallographica. Section E, Crystallographic Communications·Alexandre PoirotSuzanne Fery-Forgues

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Methods Mentioned

BETA
X-ray

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