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Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions† by Xin Chen; Yunyun Bian; Baichuan Mo; Peng Sun; Chunxia Chen; Jinsong Peng is a Materials Science article available to read on EtoBox.

What is Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions† about?

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, KMnO~4~ and KHCO~3~. 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.

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Author

Xin Chen; Yunyun Bian; Baichuan Mo; Peng Sun; Chunxia Chen; Jinsong Peng

Publisher

The Royal Society of Chemistry

Published

2020

Language

EN

Field

Materials Science (Physical Sciences)