Issue 16, 2024

Rhodium-catalysed additive-free alkoxycarbonylation of indoles: 2,4,6-trimethylbenzoic acid-based carbonate anhydrides as a versatile alkoxycarboxyl source

Abstract

We report a CO-free approach to indole-2-carboxylic esters: rhodium-catalysed C(2)-alkoxycarbonylation of indoles with 2,4,6-trimethylbenzoic acid-based carbonate anhydrides. Selective C–O bond cleavage of the anhydrides facilitates the introduction of various alkoxycarbonyl groups. Control experiments suggest that merging a rhodium catalyst and KI promotes the in situ formation of the RhI species.

Graphical abstract: Rhodium-catalysed additive-free alkoxycarbonylation of indoles: 2,4,6-trimethylbenzoic acid-based carbonate anhydrides as a versatile alkoxycarboxyl source

Supplementary files

Article information

Article type
Communication
Submitted
08 Feb 2024
Accepted
22 Mar 2024
First published
27 Mar 2024
This article is Open Access
Creative Commons BY-NC license

Org. Biomol. Chem., 2024,22, 3209-3214

Rhodium-catalysed additive-free alkoxycarbonylation of indoles: 2,4,6-trimethylbenzoic acid-based carbonate anhydrides as a versatile alkoxycarboxyl source

H. Suzuki, Y. Ito, K. Yabe, Y. Takemura and T. Matsuda, Org. Biomol. Chem., 2024, 22, 3209 DOI: 10.1039/D4OB00205A

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