A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction

Beilstein J Org Chem. 2019 Jan 31:15:291-298. doi: 10.3762/bjoc.15.26. eCollection 2019.

Abstract

Herein we report a novel palladium-catalyzed reaction that results in phenanthrene derivatives using aryl iodides, ortho-bromobenzoyl chlorides and norbornadiene in one pot. This dramatic transformation undergoes ortho-C-H activation, decarbonylation and subsequent a retro-Diels-Alder process. Pleasantly, this protocol has a wider substrate range, shorter reaction times and higher yields of products than previously reported methods.

Keywords: C–H activation; norbornadiene; palladium; phenanthrene derivatives.