Issue 25, 2024

Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

Abstract

Amines are centrally important motifs in medicinal chemistry and biochemistry, and indispensable intermediates and linchpins in organic synthesis. Despite their cross-disciplinary prominence, synthetic access to amine continues to rely on two-electron approaches based on reductions and additions of organometallic reagents, limiting their accessible chemical space and necessitating stepwise preassembly of synthetic precursors. We report herein a homogeneous photocatalytic tricomponent decarboxylative radical-mediated amine construction that enables modular access to α-branched secondary amines directly from the broad and structurally diverse chemical space of carboxylic acids in a tricomponent reaction with aldehydes and aromatic amines. Our studies reveal the key role of acridine photocatalysis acting in concert with copper and Brønsted acid catalytic processes in facilitating the previously inaccessible homogeneous photocatalytic reaction and provide a streamlined segue to a wide range of amines and nonproteinogenic α-amino acids.

Graphical abstract: Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

Supplementary files

Article information

Article type
Edge Article
Submitted
09 Apr 2024
Accepted
20 May 2024
First published
22 May 2024
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 9582-9590

Acridine photocatalysis enables tricomponent direct decarboxylative amine construction

X. Sui, H. T. Dang, A. Porey, R. Trevino, A. Das, S. O. Fremin, W. B. Hughes, W. T. Thompson, S. K. Dhakal, H. D. Arman and O. V. Larionov, Chem. Sci., 2024, 15, 9582 DOI: 10.1039/D4SC02356K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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