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C−H Bond Carboxylation with Carbon Dioxide
Author(s) -
Hong Junting,
Li Man,
Zhang Jianning,
Sun Beiqi,
Mo Fanyang
Publication year - 2019
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.201802012
Subject(s) - chemistry , carboxylation , allylic rearrangement , triple bond , double bond , medicinal chemistry , organic chemistry , catalysis
Carbon dioxide is a nontoxic, renewable, and abundant C 1 source, whereas C−H bond functionalization represents one of the most important approaches to the construction of carbon–carbon bonds and carbon–heteroatom bonds in an atom‐ and step‐economical manner. Combining the chemical transformation of CO 2 with C−H bond functionalization is of great importance in the synthesis of carboxylic acids and their derivatives. The contents of this Review are organized according to the type of C−H bond involved in carboxylation. The primary types of C−H bonds are as follows: C(sp)−H bonds of terminal alkynes, C(sp 2 )−H bonds of (hetero)arenes, vinylic C(sp 2 )−H bonds, the ipso ‐C(sp 2 )−H bonds of the diazo group, aldehyde C(sp 2 )−H bonds, α‐C(sp 3 )−H bonds of the carbonyl group, γ‐C(sp 3 )−H bonds of the carbonyl group, C(sp 3 )−H bonds adjacent to nitrogen atoms, C(sp 3 )−H bonds of o ‐alkyl phenyl ketones, allylic C(sp 3 )−H bonds, C(sp 3 )−H bonds of methane, and C(sp 3 )−H bonds of halogenated aliphatic hydrocarbons. In addition, multicomponent reactions, tandem reactions, and key theoretical studies related to the carboxylation of C−H bonds are briefly summarized. Transition‐metal‐free, organocatalytic, electrochemical, and light‐driven methods are highlighted.