Issue 4, 2024

Metal-free photocatalyzed homo- and cross-dimerizations of α-hydroxyl ketones via dual C(sp3)–H functionalization: synthesis of 2,3-dihydroxyl-1,4-butanediones

Abstract

The dimerizations of α-hydroxyl ketones at the α-carbon site have been realized in the fashion of homo- and cross-coupling, leading to the synthesis of a variety of 2,3-dihydroxyl-1,4-butadiones. This dual C–H coupling reaction proceeded under transition metal-free conditions to enable the construction of a new C(sp3)–C(sp3) bond, expanding the application space of α-hydroxyl ketones and analogous model compounds from biomass. Mechanistic studies using electron paramagnetic resonance (EPR) revealed the formation of a key α-hydroxyl carbon-radical in the reactions.

Graphical abstract: Metal-free photocatalyzed homo- and cross-dimerizations of α-hydroxyl ketones via dual C(sp3)–H functionalization: synthesis of 2,3-dihydroxyl-1,4-butanediones

Supplementary files

Article information

Article type
Research Article
Submitted
19 Oct 2023
Accepted
22 Dec 2023
First published
22 Dec 2023

Org. Chem. Front., 2024,11, 1157-1162

Metal-free photocatalyzed homo- and cross-dimerizations of α-hydroxyl ketones via dual C(sp3)–H functionalization: synthesis of 2,3-dihydroxyl-1,4-butanediones

Z. Wang, E. Tang, Q. Zhou and J. Wan, Org. Chem. Front., 2024, 11, 1157 DOI: 10.1039/D3QO01727C

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