Stereoselective Nitration of Olefins via Visible-Light-Induced Iron-Complex β-Homolysis
Ziyang Chen, Shuyang Liu, Ziyi Xu, Ziyu Gan, Ran Xu, Zhiyan Xue, Yunhe Jin
Abstract
Herein, we develop a green and efficient method for the stereoselective synthesis of nitroolefins with ferric nitrate as the nitration reagent. With a visible-light-induced iron-complex β-homolysis pathway and I – as a crucial media for electron transfer and dehydrogenation, a broad scope of nitroolefins including some valuable biorelevant derivatives are achieved in high E -selectivity. The reaction is conveniently controlled by nitrate equivalences, and scale-up experiments in batch and flow indicate excellent practicability for this protocol.
Topics & Concepts
HomolysisNitrationStereoselectivityChemistryPhotochemistryOrganic chemistryRadicalCatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques