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Issue 42, 2020, Issue in Progress
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Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions

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Abstract

Starting from arylboronic acids and ester (Z)-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(II)-catalyzed sequential Chan–Lam N-arylation and cross-dehydrogenative coupling (CDC) reactions. The initial Chan–Lam arylation can proceed in DMF at 100 °C for 24 h to give ester (Z)-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)2/tri-tert-butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO4 and KHCO3. Sequentially, these in situ arylated intermediates can undergo an intramolecular oxidative cross-dehydrogenative coupling process in mixed solvents (DMF/DMSO = 2 : 1) at 130 °C to give C3-functionalized multi-substituted indole derivatives.

Graphical abstract: Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions

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Supplementary files

Article information


Submitted
24 May 2020
Accepted
22 Jun 2020
First published
30 Jun 2020

This article is Open Access

RSC Adv., 2020,10, 24830-24839
Article type
Paper

Copper(II)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions

X. Chen, Y. Bian, B. Mo, P. Sun, C. Chen and J. Peng, RSC Adv., 2020, 10, 24830
DOI: 10.1039/D0RA04592F

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