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IF: 3.9
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Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions?

Published:30 June 2020 DOI: 10.1039/D0RA04592F PMID: 35517475
Xin Chen, Yunyun Bian, Baichuan Mo, Peng Sun, Chunxia Chen and Jinsong Peng

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.

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Procduct Name CAS Molecular Formula Supplier Price
Dimethyl sulfoxide 67-68-5 C2H6OS 1925 suppliers $5.00-$120900.00
N,N-Dimethylformamide 68-12-2 C3H7NO 1314 suppliers $11.20-$12200.00
Myristic acid 544-63-8 C14H28O2 792 suppliers $5.00-$1132.50
Copper(II) acetate 142-71-2 C2H4O2.1/2Cu 548 suppliers $5.00-$958.65
Tri-tert-butylphosphine tetrafluoroborate 131274-22-1 C12H28P.BF4 399 suppliers $4.00-$3170.00
Potassium permanganate standard solution KMnO4 2 suppliers Inquiry
Potassium bicarbonate [14C] KHCO3 1 suppliers Inquiry

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