Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions. Issue 42 (30th June 2020)

• Record Type: Journal Article
• Authors: Chen, Xin; Bian, Yunyun; Mo, Baichuan; Sun, Peng; Chen, Chunxia; Peng, Jinsong
• Is Part Of: RSC advances. Volume 10:Issue 42(2020)
• Page Start: 24830
• Page End: 24839
• Publication Date: 2020-06-30
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0ra04592f
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : One-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii )-catalyzed sequential oxidative Chan–Lam N -arylation and cross-dehydrogenative coupling (CDC) reaction. 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.