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Site‐Selective Alkenylation of Unactivated C(sp 3 )−H Bonds Mediated by Compact Sulfate Radical
Author(s) -
Ueda Mitsuhiro,
Kamikawa Kazuya,
Fukuyama Takahide,
Wang YiTing,
Wu YenKu,
Ryu Ilhyong
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202011992
Subject(s) - chemistry , alicyclic compound , steric effects , yield (engineering) , bond cleavage , substrate (aquarium) , medicinal chemistry , cleavage (geology) , sulfate , persulfate , stereochemistry , photochemistry , organic chemistry , catalysis , materials science , oceanography , fracture (geology) , metallurgy , composite material , geology
A broad variety of unactivated acyclic and alicyclic substrates cleanly undergo site‐selective alkenylation of unactivated C(sp 3 )−H bonds with 1,2‐bis(phenylsulfonyl)ethene in the presence of persulfate. This simple transformation furnishes ( E )‐2‐alkylvinylphenylsulfones in up to 88 % yield. In contrast with the previously reported decatungstate protocol, the current method is applicable to alkenylation of sterically hindered C−H bonds. This important advantage significantly broadens the substrate scope, and is attributed to the compact size of the sulfate radical employed in the C−H activation and cleavage.