Site‐Selective Alkenylation of Unactivated C(sp 3 )−H Bonds Mediated by Compact Sulfate Radical | Zendy

Ueda Mitsuhiro | Zendy; Kamikawa Kazuya | Zendy; Fukuyama Takahide | Zendy; Wang YiTing | Zendy; Wu YenKu | Zendy; Ryu Ilhyong | Zendy

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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.

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