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Issue 17, 2021
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Copper(ii)-catalysed direct C3–H esterification of indoles assisted by an N,N-bidentate auxiliary moiety

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Abstract

The regioselective direct C3-esterification of indoles with OXA is developed in an efficient reaction with carboxylic acids using the catalyst CuBr2 and oxidants Ag2CO3 and K2S2O8. The simple experimental procedure is proved to be broadly applicable to a range of substrates, including aromatic and aliphatic acids, and the corresponding products were obtained in good yields up to 87%. At the same time, it provides a valuable approach to produce C3-benzyl derivatives of indoles through reaction with benzyl carboxylic acid under the same reaction conditions.

Graphical abstract: Copper(ii)-catalysed direct C3–H esterification of indoles assisted by an N,N-bidentate auxiliary moiety

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Supplementary files

Article information


Submitted
19 Nov 2020
Accepted
25 Mar 2021
First published
26 Mar 2021

Org. Biomol. Chem., 2021,19, 3911-3924
Article type
Paper

Copper(II)-catalysed direct C3–H esterification of indoles assisted by an N,N-bidentate auxiliary moiety

Y. Pan, H. Xu, X. Hu, G. Li and J. Chen, Org. Biomol. Chem., 2021, 19, 3911
DOI: 10.1039/D0OB02301A

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