Recent Advances in Transition-metal-catalyzed C−C Bond Formation via C(sp2)−F Bond Cleavage

Liyan Fu; Qiang Chen; Yasushi Nishihara

doi:10.1002/tcr.202100053

Recent Advances in Transition-metal-catalyzed C−C Bond Formation via C(sp²)−F Bond Cleavage

Liyan Fu, Qiang Chen, Yasushi Nishihara

Research Institute for Interdisciplinary Science

Research output: Contribution to journal › Article › peer-review

17 Citations (Scopus)

Abstract

The activation of a carbon-fluorine bond is one of the most challenging topics in modern synthetic organic chemistry due to their low reactivity compared to other carbon-halogen bonds. In this review, we present the recent developments since 2015 on cross-coupling reactions that form C−C bonds via cleavage of C(sp²)−F bonds. Not only the conventional activation of C(sp²)−F bonds, but also decarbonylative or carbonyl-retentive cleavage of C(acyl)−F bonds will be introduced. This paper mainly describes new protocols for the formation of C(sp²)−C(sp³), C(sp²)−C(sp²), and C(sp²)−C(sp) bonds via transition-metal-catalyzed cleavage of C(sp²)−F bonds.

Original language	English
Journal	Chemical Record
DOIs	https://doi.org/10.1002/tcr.202100053
Publication status	Accepted/In press - 2021

Keywords

coupling reaction
C−C bond formation
C−F bond activation
decarbonylation
transition metal

ASJC Scopus subject areas

Chemistry(all)
Biochemistry
Chemical Engineering(all)
Materials Chemistry

Access to Document

10.1002/tcr.202100053

Cite this

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title = "Recent Advances in Transition-metal-catalyzed C−C Bond Formation via C(sp2)−F Bond Cleavage",

abstract = "The activation of a carbon-fluorine bond is one of the most challenging topics in modern synthetic organic chemistry due to their low reactivity compared to other carbon-halogen bonds. In this review, we present the recent developments since 2015 on cross-coupling reactions that form C−C bonds via cleavage of C(sp2)−F bonds. Not only the conventional activation of C(sp2)−F bonds, but also decarbonylative or carbonyl-retentive cleavage of C(acyl)−F bonds will be introduced. This paper mainly describes new protocols for the formation of C(sp2)−C(sp3), C(sp2)−C(sp2), and C(sp2)−C(sp) bonds via transition-metal-catalyzed cleavage of C(sp2)−F bonds.",

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AU - Chen, Qiang

AU - Nishihara, Yasushi

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AB - The activation of a carbon-fluorine bond is one of the most challenging topics in modern synthetic organic chemistry due to their low reactivity compared to other carbon-halogen bonds. In this review, we present the recent developments since 2015 on cross-coupling reactions that form C−C bonds via cleavage of C(sp2)−F bonds. Not only the conventional activation of C(sp2)−F bonds, but also decarbonylative or carbonyl-retentive cleavage of C(acyl)−F bonds will be introduced. This paper mainly describes new protocols for the formation of C(sp2)−C(sp3), C(sp2)−C(sp2), and C(sp2)−C(sp) bonds via transition-metal-catalyzed cleavage of C(sp2)−F bonds.

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