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

Chem Rec. 2021 Dec;21(12):3394-3410. doi: 10.1002/tcr.202100053. Epub 2021 Apr 14.

Authors

Liyan Fu¹, Qiang Chen¹, Yasushi Nishihara²

Affiliations

¹ Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.
² Research Institute for Interdisciplinary Science, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, 700-8530, Japan.

PMID: 33852203
DOI: 10.1002/tcr.202100053

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.

Keywords: C−C bond formation; C−F bond activation; coupling reaction; decarbonylation; transition metal.

Publication types

Review