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Expeditious and Efficient ortho-Selective Trifluoromethane-sulfonylation of Arylhydroxylamines

2022-02-28 by admin

Yue Liu,Songlin Bai,Yuanbo Du,Prof. Dr. Xiangbing Qi,Prof. Dr. Hongyin Gao

A metal- and oxidant-free, practical and efficient method for the synthesis of highly versatile and synthetically useful ortho-trifluoromethanesulfonylated anilines from arylhydroxylamines and trifluoromethanesulfinic chloride was developed. This rapid transformation proceeded smoothly with good yields and excellent ortho-selectivity in the absence of any metals or ligands. Mechanistically, the reaction comprised a noncanonical O-trifluoromethanesulfinylation of the arylhydroxylamine, and the subsequent [2,3]-sigmatropic rearrangement to afford ortho-trifluoromethanesulfonylated aniline derivatives. The practical application of this reaction was demonstrated by further conversion into a series of functional molecules under different reaction conditions.

https://doi.org/10.1002/anie.202115611

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