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铜（II）催化通过连续的Chan-Lam反应和交叉脱氢偶联反应合成多取代吲哚。

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

作者信息

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

机构信息

College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University No. 26 Hexing Road Harbin 150040 P. R. China.

Material Science and Engineering College, Northeast Forestry University No. 26 Hexing Road Harbin 150040 P. R. China

出版信息

RSC Adv. 2020 Jun 30;10(42):24830-24839. doi: 10.1039/d0ra04592f. eCollection 2020 Jun 29.

DOI:10.1039/d0ra04592f
PMID:35517475
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9055228/
Abstract

Starting from arylboronic acids and ester ()-3-aminoacrylates, one-pot syntheses of diverse indole-3-carboxylic esters have been described through copper(ii)-catalyzed sequential Chan-Lam -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 ()-3-(arylamino)acrylate intermediates in the presence of Cu(OAc)/tri--butylphosphine tetrafluoroborate, a catalytic amount of myristic acid as the additive, KMnO and KHCO. Sequentially, these 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.

摘要

从芳基硼酸和酯（）-3-氨基丙烯酸酯出发，通过铜（II）催化的连续Chan-Lam芳基化和交叉脱氢偶联（CDC）反应，已经描述了多种吲哚-3-羧酸酯的一锅法合成。最初的Chan-Lam芳基化反应可以在100℃的DMF中进行24小时，在Cu（OAc）/四氟硼酸三叔丁基膦、催化量的肉豆蔻酸作为添加剂、KMnO和KHCO存在下，得到酯（）-3-（芳基氨基）丙烯酸酯中间体。随后，这些芳基化中间体可以在130℃的混合溶剂（DMF/DMSO = 2∶1）中进行分子内氧化交叉脱氢偶联过程，得到C3-官能化的多取代吲哚衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/91efa05022cb/d0ra04592f-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/15e2cb7319b9/d0ra04592f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/0f4ed9168300/d0ra04592f-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/2a8eca446607/d0ra04592f-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/37a882700010/d0ra04592f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/91efa05022cb/d0ra04592f-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/15e2cb7319b9/d0ra04592f-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/0f4ed9168300/d0ra04592f-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/2a8eca446607/d0ra04592f-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/37a882700010/d0ra04592f-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6fdd/9055228/91efa05022cb/d0ra04592f-s4.jpg

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