Synlett
DOI: 10.1055/s-0040-1705901
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Dearomatization–Rearomatization Strategy for Palladium-Catalyzed C–N Cross-Coupling Reactions

Yatao Lang
a  The State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou, 730000, P. R. of China   Email: zenghy@lzu.edu.cn
,
Chao-Jun Li
b  Department of Chemistry and FQRNT Centre for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada   Email: cj.li@mcgill.ca
,
a  The State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Road, Lanzhou, 730000, P. R. of China   Email: zenghy@lzu.edu.cn
› Author Affiliations
We are grateful for financial support provided by the National Natural Science Foundation of China (NSFC, Grant Number 21971093), the International Joint Research Centre for Green Catalysis and Synthesis (Grant numbers 18JR3RA284 and 2016B01017), and the 111 project for support of our research. We also thank the Canada Research Chairs (CRC, Tier I) foundation, the E.B. Eddy Endowment Fund, and the Fonds de Recherche Nature et Technologies (FQRNT) for support provided to C.-J. Li.


Dedicated to Professor Barry. M. Trost on the occasion of his 80th birthday

Abstract

Substituted aromatic compounds play important roles in materials, biological agents, dyes, etc. Thus, the synthesis of substituted aromatic compounds has been a hot topic throughout the history of organic chemistry. Traditionally, the Friedel–Crafts reaction was a powerful tool for synthesizing substituted aromatic compounds. In recent decades, metal-catalyzed cross-coupling reactions were well developed via carbonheteroatom bond cleavage, however, having difficulties towards some strong bonds, such as C(Ar)–OH. To overcome such challenges, newer strategies are needed. In this review, we summarize the recent efforts in the development of dearomatization–rearomatization strategy for cross-coupling reactions via C(Ar)–O bond cleavage.

1 Introduction

2 Dearomatization–Rearomatization Strategy for Cross-Coupling of Phenols

3 Dearomatization–Rearomatization Strategy for Cross-Coupling of Biphenols

4 Dearomatization–Rearomatization Strategy for Cross-Coupling of Diphenyl Ethers

5 Dearomatization–Rearomatization Strategy for Cross-Coupling of Indoles

6 Summary



Publication History

Received: 11 July 2020

Accepted after revision: 24 July 2020

Publication Date:
07 September 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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