Enantioselective Nickel-Catalyzed Denitrogenative Transannulation En Route to N-N Atropisomers

Angew Chem Int Ed Engl. 2024 Apr 8:e202400441. doi: 10.1002/anie.202400441. Online ahead of print.ABSTRACTNickel-catalyzed transannulation reactions triggered by the extrusion of small gaseous molecules have emerged as a powerful strategy for the efficient construction of heterocyclic compounds. However, it's asymmetric synthesis remains challenging because of the difficulty in controlling stereo- and regioselectivity. Herein, we report the first nickel-catalyzed asymmetric synthesis of N-N atropisomers by the denitrogenative transannulation of benzotriazones with internal alkynes. A broad range of N-N atropisomers was obtained with excellent regio- and enantioselectivity under mild conditions. Moreover, density functional theory (DFT) calculations provided insights into the nickel-catalyzed reaction mechanism and enantioselectivity control.PMID:38587149 | DOI:10.1002/anie.202400441

Source: Angewandte Chemie - April 8, 2024 Category: Chemistry Authors: Fang-Bei Ge Chuan-Jun Lu Xiao Chen Wang Yao Mei An Yu-Kun Jiang Li-Ping Xu Ren-Rong Liu Source Type: research