Issue 15, 2025

Rh(iii)-catalyzed base-free α-arylation of iodonium ylides with arylboronic acids: modular synthesis of 5-aryl barbituric acids

Abstract

To date, the synthesis of 5-aryl barbituric acids remains challenging due to the limitations of existing methods, such as narrow substrate scope and multistep synthesis, thereby hampering their library construction for extensive drug screening. Herein, we address these challenges through developing a base-free Suzuki-type cross-coupling of barbituric acid-derived iodonium ylides. Electronically demanding substrates, particularly (poly)fluorinated and base-sensitive arylboronic acids, exhibit excellent compatibility with this approach. Moreover, our approach allows the late-stage installation of barbituric acid motifs into complex settings, which is difficult to achieve with previous methods. The utility of this approach is proved by the gram-scale synthesis, simplifying previous synthesis and formal synthesis of MMP-9 inhibitor.

Graphical abstract: Rh(iii)-catalyzed base-free α-arylation of iodonium ylides with arylboronic acids: modular synthesis of 5-aryl barbituric acids

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Article information

Article type
Research Article
Submitted
06 Feb 2025
Accepted
30 Mar 2025
First published
02 Apr 2025

Org. Chem. Front., 2025,12, 4242-4246

Rh(III)-catalyzed base-free α-arylation of iodonium ylides with arylboronic acids: modular synthesis of 5-aryl barbituric acids

M. He, S. Cai, N. Baiheti, L. Zhao, H. Tao and S. Mai, Org. Chem. Front., 2025, 12, 4242 DOI: 10.1039/D5QO00259A

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