Organic Photoredox-Catalyzed Site-Selective Alkylation of Glycine Derivatives and Peptides via Infrequent 1,2-Hydrogen Atom Transfer of Amidyl Radicals
Jinyu Hou, Hongying Fan, Xue Zhang, Xingyu Liu, Jian Chen, Guanghui Lv, Shiyun He, Li Hai, Zhongzhen Yang, Yong Wu
Abstract
Herein, we disclose a visible-light-driven photoredox-catalyzed protocol for site-selective alkylation of glycine derivatives via 1,2-hydrogen atom transfer, which is distinguished by metal free and mild conditions, high chemoselectivity, and good functional group compatibility. This protocol provides a unique approach for synthesizing valuable α,β-diamino acid derivatives. Furthermore, the potential synthetic merit of this transformation is proven by a scale-up reaction and late-stage functionalization of peptides.
Topics & Concepts
ChemistryAlkylationChemoselectivityCombinatorial chemistryPhotoredox catalysisHydrogen atomCatalysisRadicalGlycineFunctional groupOrganic chemistryPhotochemistryAmino acidPhotocatalysisGroup (periodic table)PolymerBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques