A Remarkably Efficient Fluoroalkylation of Cyclic Sulfates and Sulfamidates with PhSO2CF2H: Facile Entry into β-Difluoromethylated or β-Difluoromethylenated Alcohols and Amines

Authors

  • Chuanfa Ni,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Road, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-6128
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  • Jun Liu,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Road, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-6128
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  • Laijun Zhang,

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Road, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-6128
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  • Jinbo Hu Prof. Dr.

    1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Feng-Lin Road, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-6128
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  • Support of our work by the National Natural Science Foundation of China (20502029), the Shanghai Rising-Star Program (06QA14063), and the Chinese Academy of Sciences (Hundreds-Talent Program) is gratefully acknowledged.

Abstract

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On the fluor: Highly regioselective nucleophilic difluoromethylation of 1,2-cyclic sulfates and sulfamidates leads after selective desulfonylation to β-difluoromethylated and β-difluoromethylenated alcohols and amines (see scheme), which are highly useful building blocks in the life sciences.

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