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Org Lett. 2018 Feb 02;20(3):812-815. doi: 10.1021/acs.orglett.7b03950. Epub 2018 Jan 12.

Introduction of a Crystalline, Shelf-Stable Reagent for the Synthesis of Sulfur(VI) Fluorides.

Organic letters

Hua Zhou, Paramita Mukherjee, Rongqiang Liu, Edelweiss Evrard, Dianpeng Wang, John M Humphrey, Todd W Butler, Lise R Hoth, Jeffrey B Sperry, Sylvie K Sakata, Christopher J Helal, Christopher W Am Ende

Affiliations

  1. BioDuro , No. 233 North FuTe Road, WaiGaoQiao Free Trade Zone, Shanghai 200131, P. R. China.
  2. Pfizer Worldwide Research and Development , Eastern Point Road, Groton, Connecticut 06340, United States.
  3. Pfizer Worldwide Research and Development , 1 Portland Street, Cambridge, Massachusetts 02139, United States.
  4. Pfizer Worldwide Research and Development , 10770 Science Center Drive, San Diego, California 92121, United States.

PMID: 29327935 DOI: 10.1021/acs.orglett.7b03950

Abstract

The design, synthesis, and application of [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF), a shelf-stable, crystalline reagent for the synthesis of sulfur(VI) fluorides, is described. The utility of AISF is demonstrated in the synthesis of a diverse array of aryl fluorosulfates and sulfamoyl fluorides under mild conditions. Additionally, a single-step preparation of AISF was developed that installed the bis(fluorosulfonyl)imide group on acetanilide utilizing an oxidative C-H functionalization protocol.

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