Selective C−H Bond Functionalization of Unprotected Indoles by Donor‐Acceptor Carbene Insertion-Reference-Cited by-同舟云学术

Selective C−H Bond Functionalization of Unprotected Indoles by Donor‐Acceptor Carbene Insertion

Published:2023-09-05 Issue: Volume: Page:
ISSN:1615-4150
Container-title:Advanced Synthesis & Catalysis
language:en
Short-container-title:Adv Synth Catal

Author:

Diego Pizarro Juan¹,Morán‐González Lucía²³,González‐Fernández Iván¹,Maseras Feliu²,Fructos Manuel R.¹,Pérez Pedro J.¹

Affiliation:

1. Laboratorio de Catálisis Homogénea Unidad Asociada al CSIC CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química Universidad de Huelva 21007 Huelva Spain

2. Institute of Chemical Research of Catalonia (ICIQ-CERCA) The Barcelona Institute of Science and Technology Avgda. Països Catalans, 16 43007 Tarragona Spain

3. Departament de Química Física i Inorgànica Universitat Rovira i Virgili, c/Marcel⋅lí Domingo s/n 43007 Tarragona Spain

Abstract

AbstractCopper catalysts containing alkoxydiaminophosphine (ADAP) ligand catalyze the selective C3−H functionalization of unprotected indoles upon carbene transfer from donor‐acceptor diazo compounds, the N−H bond remaining unaltered during the transformation. Mechanistic studies, including DFT calculations, allows proposing the existence of two competitive pathways, none of them occurring through the formation of cyclopropane intermediates, at variance with previously reported systems.

Funder

Universidad de Huelva

Generalitat de Catalunya

Publisher

Wiley

Subject

General Chemistry

Link

https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.202300252

Reference73 articles.

2. M. P. Doyle M. A. McKervey T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds Wiley New York 1998;

3. Catalytic Carbene Insertion into C−H Bonds

4. Recent advances in transition-metal-catalyzed carbene insertion to C–H bonds

5. Recent Advances in Metal‐Catalyzed Functionalization of Indoles

Cited by 1 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. Mechanistic Insight into Palladium‐Catalyzed Asymmetric Alkylation of Indoles with Diazoesters Employing Bipyridine‐N,N’‐dioxides as Chiral Controllers;Advanced Synthesis & Catalysis;2023-12-06