4.8 Article

A Convenient Metal-Free Reagent for the Generation and Capture of Trifluoromethanethiol

Journal

ORGANIC LETTERS
Volume 15, Issue 22, Pages 5898-5901

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol403038f

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Funding

  1. China Scholarship Council

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0-Octadecyl-S-trifluorothiolcarbonate is a cheap and storable crystalline source of trifluoromethanethiol that can be prepared in two steps on a multigram scale from trifluoroacetic anhydride and sodium 0-octadecyl-dithiocarbonate (xanthate). It reacts directly with gramines or with alpha-bromoketones and -esters in the presence of KF and pyrrolidine to give the corresponding trifluoromethyl sulfides in generally high yield.

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