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Generation and Reactivity of Amidyl Radicals: Manganese‐Mediated Atom‐Transfer Reaction
Author(s) -
Liu RunZhou,
Li Jinxia,
Sun Jun,
Liu XianGuan,
Qu Shuanglin,
Li Ping,
Zhang Bo
Publication year - 2020
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.201913042
Subject(s) - chemistry , manganese , intramolecular force , radical , reactivity (psychology) , catalysis , combinatorial chemistry , amine gas treating , intermolecular force , substrate (aquarium) , molecule , alkyl , organic chemistry , photochemistry , medicine , oceanography , alternative medicine , pathology , geology
A simple and efficient protocol to generate amidyl radicals from amine functionalities through a manganese‐mediated atom‐transfer reaction has been developed. This approach employs an earth‐abundant and inexpensive manganese complex, Mn 2 (CO) 10 , as the catalyst and visible light as the energy input. Using this strategy, site‐selective chlorination of unactivated C(sp 3 )−H bonds of aliphatic amines and intramolecular/intermolecular chloroaminations of unactivated alkenes were readily realized under mild reaction conditions, thus providing efficient access to a range of synthetically valuable alkyl chlorides, chlorinated pyrrolidines, and vicinal chloroamine derivatives. These practical reactions exhibit a broad substrate scope and tolerate a wide array of functional groups, and complex molecules including various marketed drug derivatives.