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Issue 8, 2021
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Mangana(iii/iv)electro-catalyzed C(sp3)–H azidation

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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.

Graphical abstract: Mangana(iii/iv)electro-catalyzed C(sp3)–H azidation

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Supplementary files

Article information


Submitted
27 Oct 2020
Accepted
28 Dec 2020
First published
28 Dec 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021,12, 2890-2897
Article type
Edge Article

Mangana(III/IV)electro-catalyzed C(sp3)–H azidation

T. H. Meyer, R. C. Samanta, A. Del Vecchio and L. Ackermann, Chem. Sci., 2021, 12, 2890
DOI: 10.1039/D0SC05924B

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