Visible‐Light‐Promoted C(sp<sup>3</sup>)−H Alkylation by Intermolecular Charge Transfer: Preparation of Unnatural α‐Amino Acids and Late‐Stage Modification of Peptides
Chao Wang, Rupeng Qi, Hongxiang Xue, Yuxuan Shen, Min Chang, Yaqiong Chen, Rui Wang, Zhaoqing Xu
Abstract
)-H alkylation of glycine and peptides using Katritzky salts as electrophiles. Simple reaction conditions and excellent functional-group tolerance provide a general strategy for the efficient preparation of unnatural α-amino acids and precise modification of peptides with unnatural α-amino-acid residues. Mechanistic studies suggest that visible-light-promoted intermolecular charge transfer within a glycine-Katritzky salt electron donor-acceptor (EDA) complex induces a single-electron transfer process without the assistance of photocatalyst.
Topics & Concepts
ChemistryAlkylationElectrophileGlycineIntermolecular forceAmino acidVisible spectrumCombinatorial chemistrySalt (chemistry)AcceptorElectron transferPhotochemistryFunctional groupStereochemistryOrganic chemistryCatalysisMoleculeBiochemistryOptoelectronicsCondensed matter physicsPhysicsPolymerRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques