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HERO ID
7676166
Reference Type
Journal Article
Title
Chemoselective Hydro(Chloro)pentafluorosulfanylation of Diazo Compounds with Pentafluorosulfanyl Chloride
Author(s)
Qing, FL; Shou, JY; Xu, XH
Year
2021
Is Peer Reviewed?
Yes
Journal
Angewandte Chemie (International Edition)
ISSN:
1433-7851
EISSN:
1521-3773
Publisher
John Wiley and Sons Inc
Language
English
PMID
33928731
DOI
10.1002/anie.202103606
Abstract
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 relied on hazardous reagents and specialized apparatuses. 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.
Keywords
copper; diazo compounds; pentafluorosulfanyl chloride; pentafluorosulfanylation; radical reactions
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