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Synthesis 2016; 48(24): 4381-4399
DOI: 10.1055/s-0035-1562795
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Progress on Copper-Mediated Directing-Group-Assisted C(sp2)–H Activation

Ming Shang
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
,
Shang-Zheng Sun
b   Department of Chemistry, Innovative Drug Research Center, Shanghai University, 99 Shangda Road, 200444, P. R. of China   Email: hxdai@sioc.ac.cn
,
Hong-Li Wang
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
,
Ming-Ming Wang
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
,
Hui-Xiong Dai*
a   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
› Author Affiliations
Further Information

Publication History

Received: 24 April 2016

Accepted after revision: 07 July 2016

Publication Date:
09 September 2016 (online)

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Abstract

Considerable progress has been made in the area of copper-mediated C(sp2)–H functionalization reactions with the assistance of chelating directing groups. Due to the advantages of copper catalysts such as low cost, low toxicity, and unique reactivity compared to precious metals, they have attracted more and more attention in organic synthesis. This review summarizes recent advances in this field according to the classification of directing groups.

1 Introduction

2 The Pyridine Directing Group

2.1 C–N Bond Formation

2.2 C–O Bond Formation

2.3 C–S Bond Formation

2.4 C–C Bond Formation

2.5 C–CN Bond Formation

2.6 C–Halogen Bond Formation

3 Bidentate Directing Groups

3.1 8-Aminoquinoline

3.2 (2-Pyridyl)Sulfonyl and Picolinic Acid

3.3 Amide-Oxazoline Auxiliary

3.4 2-(Pyridin-2-yl)isopropylamine (PIP Amine)

3.5 2-Aminopyridine 1-Oxide

4 Conclusions and Outlook

Key words

C–H bond functionalization - copper - pyridine - bidentate directing group
 

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