Phosphoric Acid Mediated Light‐Induced Minisci C−H Alkylation of <i>N</i>‐Heteroarenes
Songyang Jin, Xinxin Geng, Yujun Li, Ke Zheng
Abstract
Abstract Herein, we report an environmentally‐friendly light‐induced Minisci alkylation of N ‐heteroarenes with a broad substrate scope using diphenyl phosphate as catalyst under metal‐ and photocatalyst‐free conditions. The radical precursor redox‐active esters (RAEs) were introduced as alkylating reagents for the functionalization of N ‐heteroarene derivatives including pyridine, quinoline, and isoquinoline. Mechanistic studies suggested that diphenyl phosphate played a key role via hydrogen bonding in the catalytic cycle.
Topics & Concepts
ChemistryIsoquinolineAlkylationQuinolineCatalysisPhosphoric acidPhotoredox catalysisReagentPhotocatalysisCombinatorial chemistryPyridineOrganocatalysisSubstrate (aquarium)RadicalOrganic chemistryEnantioselective synthesisGeologyOceanographyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques