Ni(II)-catalyzed oxidative coupling between C(sp(2))-H in benzamides and C(sp(3))-H in toluene derivatives

Yoshinori Aihara; Mamoru Tobisu; Yoshiya Fukumoto; Naoto Chatani

doi:10.1021/ja5095342

Ni(II)-catalyzed oxidative coupling between C(sp(2))-H in benzamides and C(sp(3))-H in toluene derivatives

J Am Chem Soc. 2014 Nov 5;136(44):15509-12. doi: 10.1021/ja5095342. Epub 2014 Oct 27.

Authors

Yoshinori Aihara¹, Mamoru Tobisu, Yoshiya Fukumoto, Naoto Chatani

Affiliation

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

PMID: 25347731
DOI: 10.1021/ja5095342

Abstract

Oxidative coupling between C(sp(2))-H bonds and C(sp(3))-H bonds is achieved by the Ni(II)-catalyzed reaction of benzamides containing an 8-aminoquinoline moiety as the directing group with toluene derivatives in the presence of heptafluoroisopropyl iodide as the oxidant. The method has a broad scope and shows high functional group compatibility. Toluene derivatives can be used as the coupling partner in an unreactive solvent.