Conversion of Phenols and Anilines to trans-Olefins via Oxidation, Wittig Olefination, and Stereoselective Olefin Isomerization

Abstract

Development of metal-free conversion of naturally abundant phenols and anilines to the corresponding olefins remains a formidable challenge. The current state of the art relies on the TM-catalyzed Heck coupling of activated phenols (triflates, tosylates, and more) with the olefins. While these advancements are promising, the reaction suffers from branch vs linear selectivity and requires an expensive TM−ligand combination, hazardous organotin reagents, and very high reaction temperature. Herein, we reported a one-pot conversion of phenol and anilines to the corresponding E-olefins, which goes via oxidation, Wittig olefination, and stereoselective olefin isomerization.