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Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji–Trost of Benzotriazoles with 1,3-Dienes by Yin-Lin Li; Pei-Chao Zhang; Hai-Hong Wu; Junliang Zhang is a Chemistry article available to read on EtoBox.

What is Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji–Trost of Benzotriazoles with 1,3-Dienes about?

The asymmetric denitrogenative cycloaddition has emerged as a powerful tool to build chiral aza-heterocyles. However, only one example of asymmetric denitrogenative cycloaddition of benzotriazole with unsaturated hydrocarbons has been explored so far, because the ring-opening of benzotriazole to generate α-imino metal carbenoid species is a thermodynamically unfavorable process. We herein report an efficient asymmetric denitrogenative cycloaddition of benzotriazoles with cyclic and acyclic 1,3-dienes enabled by Pd and chiral sulfonamide phosphine ligand. A variety of substituted hexahydrocarbazoles and indolines were delivered in good yields with high ee values. Interestingly, a pair of enantiomers could be obtained with the use of Xu1 and PC2 with the same absolute configuration. The synthetic utilities of the optically active hexahydrocarbazoles were also showcased. T ransition metal-catalyzed asymmetric denitrogenative cycloaddition has emerged as a powerful tool to build chiral aza-heterocyles (Scheme 1a). 1 In this regard, Fokin and co-workers reported the earliest use of chiral Rh catalysts for such asymmetric reactions of 1,2,3-triazoles with various unsaturated compounds. 2

Who reads Palladium-Catalyzed Asymmetric Tandem Denitrogenative Heck/Tsuji–Trost of Benzotriazoles with 1,3-Dienes?

Author

Yin-Lin Li; Pei-Chao Zhang; Hai-Hong Wu; Junliang Zhang

Publisher

American Chemical Society (ACS)

Published

2021

Language

EN

Field

Chemistry (Physical Sciences)