YAO Hequan and LIN Aijun Team Report New Progress in Palladium-catalyzed Remote 1,N-aryl Amination

Release date:2019-04-18  Release:主页英文版


Recently, ACS Catalysis (impact factor 11.384), the top journal of the American Chemical Society, published online the latest research in the transition metal palladium catalyzed remote 1,1 -carbonation of non-activated olefins reported by Professor YAO Hequan and Professor LIN Aijun from the Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University——Palladium-catalyzed Remote 1,n-Arylamination of Unactivated Terminal Alkenes. Ph.D. student HAN Chunhua is the first author of this article. Professor YAO Hequan and Professor LIN Aijun are the correspondent authors of this article.

The olefin skeleton is widely present in natural products, pharmaceutically active molecules and functional material molecules. It is not only an important component of the construction of compounds, but also an important research object for the later structural modification and modification of compounds to improve activity and functionality. In addition, the olefin skeleton can be produced quickly and conveniently by conversion of various other functional groups. Therefore, in the past few decades, the selective 1,2-difunctionalization of olefins, especially the 1,2-carbon amination of olefins, has attracted widespread attention among chemists in the fields of organic synthetic chemistry and medicinal chemistry and has developed rapidly. However, due to the lack of effective synthetic strategies to control more complex regioselectivity and chemoselectivity, the long-term 1, n-bifunctionalization (including 1, n-carbonation) reaction of olefins has been slow and faced major challenges. In this research work, the researchers skillfully utilized transition metal palladium to catalyze Heck arylation, olefin isomerization and aza-Michael addition, and successfully achieved long-range 1, n-aryl amination of non-activated olefins for the first time (n3). The reaction has high regioselectivity, chemical selectivity and broad spectrum substrate suitability.

The results of this research provide a new idea and synthesis method for the extensive and in-depth study of the remote bifunctionalization of inactive olefins and the efficient construction of complex functional nitrogenous compounds.

The work was supported by the National Natural Science Foundation of China, the National Key Laboratory of Natural Medicine Active Components and Pharmacodynamic Innovation Research and Cultivation Project, and the Double-Class Construction Project of China Pharmaceutical University.