Photoinduced Metal-Free α-C(sp<sup>3</sup>)–H Carbamoylation of Saturated <i>Aza</i>-Heterocycles via Rationally Designed Organic Photocatalyst
Mingjun Yi, Huan-Xin Zhang, Tengfei Xiao, Jihua Zhang, Zhitao Feng, Li‐Pu Wei, Guo‐Qiang Xu, Peng‐Fei Xu
Abstract
Herein, we report a general strategy for the rational design of an efficient organic photocatalyst, and we describe a robust method for the direct C(sp3)–H carbamoylation of saturated aza-heterocycles under mild conditions by using a naphthalimide (NI)-based organic photocatalyst. This protocol provides a concise and practical approach for the rapid installation of a valuable amide bond onto pharmaceutically useful saturated aza-heterocycles to access a wide range of cyclic α-amino amides. A series of mechanism investigations have demonstrated this transformation undergoes a visible-light photocatalytic, oxidative Ugi reaction process.
Topics & Concepts
PhotocatalysisAmideChemistryCombinatorial chemistryCatalysisRational designMetalPhotochemistryOrganic chemistryMaterials scienceNanotechnologyCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesSynthesis and Catalytic Reactions