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Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride
Author(s) -
Shou JiaYi,
Xu XiuHua,
Qing FengLing
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202103606
Subject(s) - diazo , reagent , chemistry , chloride , hexane , combinatorial chemistry , organic chemistry , organic synthesis , catalysis
Pentafluorosulfanyl chloride (SF 5 Cl) is the most prevalent reagent for the incorporation of SF 5 group into organic compounds. However, the preparation of SF 5 Cl often relies on hazardous reagents and specialized apparatus. Herein, we described a safe and practical synthesis of a bench‐stable and easy‐to‐handle solution of SF 5 Cl in n ‐hexane under gas‐reagent‐free conditions. The synthetic application of SF 5 Cl was demonstrated through the unprecedented reaction with diazo compounds. The chemoselective hydro‐ and chloropentafluorosulfanylations of α‐diazo carbonyl compounds were developed in the presence of K 3 PO 4 or copper catalyst, respectively. These reactions provide a direct and efficient access to various α‐pentafluorosulfanyl carbonyl compounds of high value for potential applications.