Iron-Catalyzed <i>Ipso</i>-Nitration of Aryl Borides via Visible-Light-Induced β-Homolysis
Shuyang Liu, Shuyang Liu, Yusheng Lu, Hongyao Wang, Zhiyan Xue, Ziyi Xu, Huihui Wan, Qingxin Yin, Tianming Lv, Shu-Xin Liu, Shu-Xin Liu, Yunhe Jin
Abstract
High Resolution Image Download MS PowerPoint Slide Herein, we reported a practical method to realize ipso -nitration of boronic acids, their pinacol esters, and trifluoroborate salts with alkali metal salt NaNO 3 as a nitrating reagent. A Fe III /Fe IV catalytic cycle involving an unusual visible-light-induced β-homolysis pathway of the N–O bond in a simple iron complex effectively provides a nitryl radical as the key nitrating species. This protocol bears mild reaction conditions, a broad scope (up to 99% yield), good functional group compatibility, and convenient scale-up synthesis.
Topics & Concepts
HomolysisCatalysisNitrationArylVisible spectrumChemistryPhotochemistryBenzimidazoleCombinatorial chemistryOrganic chemistryMaterials scienceRadicalAlkylOptoelectronicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions