Synthesis of Phenylpropanoids via Matsuda-Heck Coupling of Arene Diazonium Salts

J Org Chem. 2017 Apr 21;82(8):4386-4395. doi: 10.1021/acs.joc.7b00447. Epub 2017 Apr 13.

Abstract

The Pd-catalyzed Heck-type coupling (Matsuda-Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A and C.