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. 2018 Feb 5;57(6):1688-1691.
doi: 10.1002/anie.201711968. Epub 2018 Jan 10.

Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes

Tung Thanh Nguyen  1 , Liene Grigorjeva  1 , Olafs Daugulis  1
Affiliations

Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes

Tung Thanh Nguyen et al. Angew Chem Int Ed Engl. .

Abstract

A method for cobalt-catalyzed, carboxylate-directed functionalization of arene C-H bonds is reported. Alkynes, styrenes, and 1,3-dienes can be coupled with benzoic acids to provide cyclic products in good yields. The reactions proceed in the presence of a cobalt(II) hexafluoroacetylacetonate catalyst, (TMS)2 NH base, Ce(SO4 )2 cooxidant, and oxygen oxidant.

Keywords: C−H activation; alkenylation; benzoic acid; cobalt; olefin.

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Conflict of interest statement

Conflict of interest

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
Carboxylic acid C–H bond functionalization. 1→2: Pd for sp3 C–H; Pd, Ir, Rh, Ru for sp2 C–H bonds, many examples; Fe, Co, two examples, limited scope. 1→3→4→2: sp2 and sp3 C–H; Cu, Fe, Co, Ni, Ru, Rh, Pd; many examples.
Scheme 2
Scheme 2
Mechanistic considerations.
See this image and copyright information in PMC

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