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Selective C( sp 3 )−H Functionalization of Alkyl Esters with N ‐/ S ‐/ O ‐Nucleophiles Using Perfluoroalkyl Iodide as Oxidant
Author(s) -
Zhao ShiWen,
Cai SongZhou,
Wang MaoLin,
Rao Weidong,
Xu Haiyan,
Zhang Lei,
Chu XueQiang,
Shen ZhiLiang
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000199
Subject(s) - chemistry , amination , nucleophile , alkyl , iodide , surface modification , organic chemistry , medicinal chemistry , bond cleavage , halogenation , phenols , reagent , substrate (aquarium) , combinatorial chemistry , catalysis , oceanography , geology
An efficient transition metal‐free approach to achieve the selective cleavage of the α‐carbonyl C( sp 3 )−H bond in alkyl esters by using inexpensive, low‐toxic, and insensitive perfluoroalkyl iodide as the radical initiator has been developed. A variety of enamides, N ‐heterocycles, amides, thiophenols, and phenols could be successfully incorporated into functionalized alkyl groups by intermolecular amination, thioetherification, and etherification. The distinguishing features of this CDC reaction are its broad substrate scope, synthetic simplicity, and mild reaction conditions.