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Site- and Enantioselective Manganese-Catalyzed Benzylic C–H Azidation of Indolines by Min Cao; Hongliang Wang; Yingang Ma; Chen-Ho Tung; Lei Liu is a Chemistry article available to read on EtoBox.

What is Site- and Enantioselective Manganese-Catalyzed Benzylic C–H Azidation of Indolines about?

A manganese-catalyzed highly site- and enantioselective benzylic C-H azidation of indolines has been described. The practical method is applicable for azidation of a tertiary benzylic C-H bond with good functional group tolerance, allowing facile access to structurally diverse tertiary azide-containing indolines in high efficiency with excellent site-, chemo-, and enantioselectivity. The generality of the method was further demonstrated by site- and enantioselective azidation of the secondary benzylic C-H bond for a range of secondary azide-containing indolines. The benzylic C-H azidation method allows to straightforwardly and enantioselectively install a variety of nitrogen-based functional groups and diverse bioactive molecules at the C position of indoline frameworks through post-azidation manipulations. Gram-scale synthesis was also demonstrated, further highlighting the synthetic potential of the method. Mechanistic studies by combined experiments and computations elucidated the reaction mechanism and origins of stereoselectivity.

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Author

Min Cao; Hongliang Wang; Yingang Ma; Chen-Ho Tung; Lei Liu

Publisher

American Chemical Society (ACS)

Published

2022

Language

EN

Field

Chemistry (Physical Sciences)