Abstract: Transition metal-catalyzed carbon-heteroatom bond formation is a crucial area in synthetic organic chemistry. The Kharasch-Sosnovsky reaction, catalyzed by copper, facilitates the conversion of olefins to allylic esters using tert-butyl peroxybenzoate as both an oxidant and oxygen source. In line with the “National Dual-Carbon Strategy”, the development of green and efficient catalytic systems for carbon-based transformations has become a key focus in organic chemistry. In this context, the Kharasch-Sosnovsky-type reaction has witnesses notable advances regarding asymmetric versions, ligand design, substrate scope expansion, and sustainable conditions. By surveying the cutting-edge chemical research, this paper presents a concise overview of the discovery and new progress of Kharasch-Sosnovsky reaction. It is hoped that this review can not only enhance students’ comprehension of fundamental organic chemistry concepts, but also effectively fill the gaps in existing textbooks, achieving a deep integration of basic chemical knowledge with cutting-edge research in the discipline.

Key words: Kharasch-Sosnovsky reaction, Copper catalysis, Olefin oxidation, Asymmetric radical reaction