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Copper-Catalyzed Arylation of Remote C(sp 3 )-H Bonds in Carboxamides and Sulfonamides

Copper-Catalyzed Arylation of Remote C(sp 3 )-H Bonds in Carboxamides and Sulfonamides

Zhaodong Li, Qian Wang, Jieping Zhu

Angew Chem Int Ed Engl. 2018 Oct 1;57(40):13288-13292.

PMID: 30113116

Abstract:

Reported herein is an unprecedented copper-catalyzed arylation of remote C(sp3 )-H bonds. Stirring a trifluorotoluene solution of either N-fluorocarboxamides or N-fluorosulfonamides and arylboronic acids in the presence of a catalytic amount of copper(II) trifluoroacetylacetonate, 2,2'-bipyridine, and sodium tert-butoxide afforded the γ- and δ-C(sp3 )-H arylated carboxamides and sulfonamides, respectively, in good to high yields. Mechanistic studies indicate that the reaction might proceed through an amidyl radical generation, 1,5-hydrogen atom transfer (HAT), and copper-catalyzed cross-coupling of the resulting carbon radical with arylboronic acids.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP14324824	Copper(II) trifluoroacetylacetonate		14324-82-4	Price

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