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A Broad‐Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates **
Author(s) -
Wei Mingjie,
Liang Dacheng,
Cao Xiaohui,
Luo Wenjun,
Ma Guojian,
Liu Zeyuan,
Li Le
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202013976
Subject(s) - sulfonyl , catalysis , broad spectrum , chemistry , steric effects , combinatorial chemistry , fluoride , derivative (finance) , organic chemistry , inorganic chemistry , alkyl , financial economics , economics
Abstract A broad‐spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1‐hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for sterically hindered substrates. Catalyst loading is generally low and only 0.02 mol % of catalyst is required for the multidecagram‐scale synthesis of an amantadine derivative. In addition, the potential of this method in medicinal chemistry has been demonstrated by the synthesis of the marketed drug Fedratinib via a key intermediate sulfonyl fluoride 13 . Since a large number of amines are commercially available, this route provides a facile entry to access Fedratinib analogues for biological screening.