Pd/PC-Phos-Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N-Allenamides
Pei-Chao Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorJie Han
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Junliang Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438 P. R. China
Search for more papers by this authorPei-Chao Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorJie Han
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Junliang Zhang
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062 P. R. China
Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438 P. R. China
Search for more papers by this authorGraphical Abstract
The first example of an enantioselective denitrogenative cyclization of benzotriazoles with allenes and N-allenamides is enabled using Pd/PC-Phos catalysis, and provides rapid access to optically active 3-methyleneindolines in good yields with high ee values. The method features a general substrate scope, high regioselectivity, and mild reaction conditions. Tf=trifluoromethanesulfonyl.
Abstract
Reported herein is an asymmetric Pd/PC-Phos-catalyzed denitrogenative cyclization of benzotriazoles with allenes and N-allenamides, representing the first example of enantioselective denitrogenative cyclizations of benzotriazoles. A series of optically active 3-methyleneindolines were obtained in good yields with high ee values. The use of inexpensive and readily available starting materials, high regio- and enantioselectivity, a broad substrate scope, mild reaction conditions, no need for base, as well as versatile functionalization of the 3-methyleneindolines make this approach attractive.
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