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Mangana(iii/iv)electro-catalyzed C(sp³)-H azidation.

ABSTRACT: Manganaelectro-catalyzed azidation of otherwise inert C(sp³)-H bonds was accomplished using most user-friendly sodium azide as the nitrogen-source. The operationally simple, resource-economic C-H azidation strategy was characterized by mild reaction conditions, no directing group, traceless electrons as the sole redox-reagent, Earth-abundant manganese as the catalyst, high functional-group compatibility and high chemoselectivity, setting the stage for late-stage azidation of bioactive compounds. Detailed mechanistic studies by experiment, spectrophotometry and cyclic voltammetry provided strong support for metal-catalyzed aliphatic radical formation, along with subsequent azidyl radical transfer within a manganese(iii/iv) manifold.

SUBMITTER: Meyer TH

PROVIDER: S-EPMC8179422 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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Mangana(iii/iv)electro-catalyzed C(sp3)-H azidation.

Meyer Tjark H TH Samanta Ramesh C RC Del Vecchio Antonio A Ackermann Lutz L

Chemical science 20201228 8

Manganaelectro-catalyzed azidation of otherwise inert C(sp3)-H bonds was accomplished using most user-friendly sodium azide as the nitrogen-source. The operationally simple, resource-economic C-H azidation strategy was characterized by mild reaction conditions, no directing group, traceless electrons as the sole redox-reagent, Earth-abundant manganese as the catalyst, high functional-group compatibility and high chemoselectivity, setting the stage for late-stage azidation of bioactive ...[more]

PMID: 34164055

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