Issue 26, 2021

Alkylation of the α-amino C–H bonds of anilines photocatalyzed by a DMEDA-Cu-benzophenone complex: reaction scope and mechanistic studies

Abstract

The Cu(II) complex 1 incorporating a BP chromophore is a highly active and chemoselective photocatalyst for the alkylation of α-amino C–H bonds of anilines. The reaction was shown to proceed with a broad substrate scope in the absence of additives. Extensive mechanistic studies were performed, in particular using transient absorption spectroscopy, and spectroscopic signatures of key intermediates were identified in the conditions of catalysis. Finally, the ability of 1 to act as a multitask catalyst was showcased by conducting multi-component CuAAC and olefin hydroalkylation reactions in one-pot.

Graphical abstract: Alkylation of the α-amino C–H bonds of anilines photocatalyzed by a DMEDA-Cu-benzophenone complex: reaction scope and mechanistic studies

Supplementary files

Article information

Article type
Paper
Submitted
17 May 2021
Accepted
04 Jun 2021
First published
04 Jun 2021

Org. Biomol. Chem., 2021,19, 5800-5805

Alkylation of the α-amino C–H bonds of anilines photocatalyzed by a DMEDA-Cu-benzophenone complex: reaction scope and mechanistic studies

B. Abadie, G. Jonusauskas, N. D. McClenaghan, P. Y. Toullec and J. Vincent, Org. Biomol. Chem., 2021, 19, 5800 DOI: 10.1039/D1OB00960E

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