Palladium-Catalyzed Cascade Reaction of o-Cyanobiaryls with Arylboronic Acids: Synthesis of 5-Arylidene-7-aryl-5 H-dibenzo[ c, e]azepines

Org Lett. 2019 Oct 4;21(19):7697-7701. doi: 10.1021/acs.orglett.9b02351. Epub 2019 Aug 8.

Abstract

A palladium-catalyzed cascade reaction of 2'-acetyl-[1,1'-biphenyl]-2-carbonitriles with arylboronic acids is developed. This reaction affords a new class of seven-membered 5-arylidene-7-aryl-5H-dibenzo[c,e]azepines with good functional group compatibility and selectivity. Reaction mechanistic study suggests that this transformation involves carbopalladation of nitrile and subsequent intramolecular cyclization followed by oxidative Heck coupling.