Free-Radical-Promoted Remote Unactivated C(sp<sup>3</sup>)–H Dehydrogenative Coupling Reaction of Free Alcohols with Quinone and Chromone
Zhengbao Xu, Yameng Gao, Shanshan Wang, Qili Zhang, Lizhi Zhang, Liang Shen
Abstract
An efficient free-radical-promoted unactivated C(sp3)–H dehydrogenative coupling reaction of free alcohols at the δ position with quinone and chromone has been developed. This reaction has a good functional group tolerance and substrate scope; various alcohols reacted with quinones and chromones to give the corresponding C(sp2)–H alkylation products in moderate to good yields. A gram-scale experiment can be successfully operated. This protocol provides a sustainable and practical strategy for the late-stage functionalization of alcohols with quinones and chromones by constructing the challenging δ-selective C(sp3)–C(sp2) bond.
Topics & Concepts
ChromoneChemistrySubstrate (aquarium)QuinoneFunctional groupCoupling reactionFree-radical reactionCombinatorial chemistryRadicalOrganic chemistryReaction conditionsMedicinal chemistryPhotochemistryCatalysisGeologyPolymerOceanographyCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsRadical Photochemical Reactions