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Review
. 2015 Nov 9:11:2132-44.
doi: 10.3762/bjoc.11.230. eCollection 2015.

C-H bond halogenation catalyzed or mediated by copper: an overview

Wenyan Hao  1 , Yunyun Liu  1
Affiliations
Review

C-H bond halogenation catalyzed or mediated by copper: an overview

Wenyan Hao et al. Beilstein J Org Chem. .

Abstract

Carbon-halogen (C-X) bonds are amongst the most fundamental groups in organic synthesis, they are frequently and widely employed in the synthesis of numerous organic products. The generation of a C-X bond, therefore, constitutes an issue of universal interest. Herein, the research advances on the copper-catalyzed and mediated C-X (X = F, Cl, Br, I) bond formation via direct C-H bond transformation is reviewed.

Keywords: C(sp2)–H bond; C(sp3)–H bond; copper; halogenation.

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Figures

Scheme 1
Scheme 1
Copper-catalyzed C–H bond halogenation of 2-arylpyridine.
Scheme 2
Scheme 2
ortho-Chlorination of 2-arylpridines with acyl chlorides.
Scheme 3
Scheme 3
Copper-catalyzed chlorination of 2-arylpyridines using LiCl.
Scheme 4
Scheme 4
Copper-catalyzed C–H halogenation of 2-arylpyridines using LiX.
Scheme 5
Scheme 5
Copper-mediated selective C–H halogenations of 2-arylpyridine.
Scheme 6
Scheme 6
Copper-catalyzed C–H o-halogenation using removable DG.
Scheme 7
Scheme 7
Copper-catalyzed C–H halogenations using PIP as DG.
Scheme 8
Scheme 8
Copper-catalyzed quinoline C–H chlorination.
Scheme 9
Scheme 9
Copper-catalyzed arene C–H fluorination of benzamides.
Scheme 10
Scheme 10
Copper-catalyzed arene C–H iodination of 1,3-azoles.
Scheme 11
Scheme 11
Copper-catalyzed C–H halogenations of phenols.
Scheme 12
Scheme 12
Proposed mechanism for the C–H halogenation of phenols.
Scheme 13
Scheme 13
Copper-catalyzed halogenation of electron enriched arenes.
Scheme 14
Scheme 14
Copper-catalyzed C–H bromination of arenes.
Scheme 15
Scheme 15
CuI-mediated synthesis of iododibenzo[b,d]furans via C–H functionalization.
Scheme 16
Scheme 16
Cu-Mn spinel oxide-catalyzed phenol and heteroarene halogenation.
Scheme 17
Scheme 17
Copper-catalyzed halogenations of 2-amino-1,3thiazoles.
Scheme 18
Scheme 18
Copper-mediated chlorination and bromination of indolizines.
Scheme 19
Scheme 19
Copper-catalyzed three-component synthesis of bromoindolizines.
Scheme 20
Scheme 20
Copper-mediated C–H halogenation of azacalix[1]arene[3]pyridines.
Scheme 21
Scheme 21
Copper-mediated cascade synthesis of halogenated pyrrolones.
Scheme 22
Scheme 22
Copper-mediated alkene C–H chlorination in spirothienooxindole.
Scheme 23
Scheme 23
Copper-catalyzed remote C–H chlorination of alkyl hydroperoxides.
Scheme 24
Scheme 24
Copper-catalyzed C–H fluorination of alkanes.
Scheme 25
Scheme 25
Copper-catalyzed or mediated C–H halogenations of active C(sp3)-bonds.
See this image and copyright information in PMC

References

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