A Highly Regioselective C-3 Benzylation Reaction of Indoles with Alcohols Catalysed by an N-Heterocyclic Carbene-Reference-Cited by-同舟云学术

A Highly Regioselective C-3 Benzylation Reaction of Indoles with Alcohols Catalysed by an N-Heterocyclic Carbene

Published:2015-08 Issue:8 Volume:39 Page:438-441
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Zhu Yan-fang¹,Lu Guo-ping¹,Cai Chun¹

Affiliation:

1. School of Chemical Engineering, Nanjing University of Science and Technology, 200 Xiaoling Wei, Nanjing 210094, P.R. China

Abstract

The direct C-3 alkylation of indoles with primary and secondary alcohols through the combination of KOH and an N-heterocyclic carbene is described. The KOH/NHC-catalysed system can give desired C-3 alkylated indoles with high selectivity in moderate to excellent yields. Moreover, this process has obvious advantages such as high atom economy and the absence of a metal source.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751915X14376593652711

Reference39 articles.

1. New Indole-Containing Medicinal Compounds

2. Mechanisms and Therapeutic Implications of Cell Death Induction by Indole Compounds

3. Drug-induced inhibition of tubulin polymerization induces mitochondrion-mediated apoptosis in yeast

4. Electrophilic Allylations and Benzylations of Indoles in Neutral Aqueous or Alcoholic Solutions

5. Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes

Cited by 7 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Multi-hydroxyl POSS supported iridium complexes as a recyclable catalyst for selective synthesis of N-/C-substituted indoles and the total synthesis of HIV-1 fusion inhibitor;Journal of Catalysis;2024-01

2. Visible-light-mediated radical reactions of indoles withpara-quinone methides using eosin Y as an organophotoredox catalyst;Organic & Biomolecular Chemistry;2023

3. Molecular Iodine-Catalyzed Selective C-3 Benzylation of Indoles with Benzylic Alcohols: A Greener Approach toward Benzylated Indoles;ACS Omega;2019-07-08

4. Base‐Mediated Transition‐Metal‐Free Dehydrative C−C and C−N Bond‐Forming Reactions from Alcohols;The Chemical Record;2019-04-25

5. Aromatic Substitution;Organic Reaction Mechanisms Series;2019-03-07