Direct arylation of C(sp3)-H bonds in aliphatic amides with diaryliodonium salts in the presence of a nickel catalyst

Miki Iyanaga; Yoshinori Aihara; Naoto Chatani

doi:10.1021/jo501691f

Direct arylation of C(sp3)-H bonds in aliphatic amides with diaryliodonium salts in the presence of a nickel catalyst

J Org Chem. 2014 Dec 19;79(24):11933-9. doi: 10.1021/jo501691f. Epub 2014 Sep 4.

Authors

Miki Iyanaga¹, Yoshinori Aihara, Naoto Chatani

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

PMID: 25162768
DOI: 10.1021/jo501691f

Abstract

The Ni(II)-catalyzed direct arylation of C(sp(3))-H (methyl and methylene) bonds in aliphatic amides containing an 8-aminoquinoline moiety as the directing group with diaryliodonium salts as coupling electrophiles is described. A wide variety of functional groups are tolerated in the reaction. The reaction represents the first example of the Ni-catalyzed direct arylation of C(sp(3))-H bonds with diaryliodonium salts.