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Visible‐Light Photoredox‐Catalyzed Ring‐Opening Carboxylation of Cyclic Oxime Esters with CO 2
Author(s) -
Jiang YuanXu,
Chen Liang,
Ran ChuanKun,
Song Lei,
Zhang Wei,
Liao LiLi,
Yu DaGang
Publication year - 2020
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202002032
Subject(s) - carboxylation , oxime , chemistry , catalysis , substrate (aquarium) , photochemistry , functional group , radical , ring (chemistry) , bond cleavage , visible spectrum , combinatorial chemistry , organic chemistry , materials science , polymer , oceanography , optoelectronics , geology
The carboxylation of cyclic oxime esters with carbon dioxide via visible‐light photoredox catalysis is demonstrated for the first time. A variety of cyclic oxime esters undergo ring‐opening C−C bond cleavage and carboxylation to give cyanoalkyl‐containing carboxylic acids in moderate to good yields. Moreover, this methodology features mild reaction conditions (room temperature, 1 atm), wide substrate scope, good functional group tolerance as well as facile derivations of products. Mechanistic studies indicate that the benzylic radicals and anions might be the key intermediates.