CC BY 4.0 · Synthesis 2017; 49(20): 4586-4598
DOI: 10.1055/s-0036-1588536
short review
Copyright with the author

Recent Advances in Transition-Metal-Catalyzed, Directed Aryl C–H/N–H Cross-Coupling Reactions

Martyn C. Henry
WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, United Kingdom   Email: [email protected]
,
Mohamed A. B. Mostafa
WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, United Kingdom   Email: [email protected]
,
WestCHEM, School of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow, G12 8QQ, United Kingdom   Email: [email protected]
› Author Affiliations
Martyn C. Henry is supported by an EPSRC DTA studentship (EP/M508056/1).
Further Information

Publication History

Received: 06 July 2017

Accepted: 14 July 2017

Publication Date:
28 August 2017 (online)


Abstract

Amination and amidation of aryl compounds using a transition-metal-catalyzed cross-coupling reaction typically involves prefunctionalization or preoxidation of either partner. In recent years, a new class of transition-metal-catalyzed cross-dehydrogenative coupling reaction has been developed for the direct formation of aryl C–N bonds. This short review highlights the substantial progress made for ortho-C–N bond formation via transition-metal-catalyzed chelation-directed aryl C–H activation and gives an overview of the challenges that remain for directed meta- and para-selective reactions.

1 Introduction

2 Intramolecular C–N Cross-Dehydrogenative Coupling

2.1 Nitrogen Functionality as Both Coupling Partner and Directing Group

2.2 Chelating-Group-Directed Intramolecular C–N Bond Formation

3 Intermolecular C–N Cross-Dehydrogenative Coupling

3.1 ortho-C–N Bond Formation

3.1.1 Copper-Catalyzed Reactions

3.1.2 Other Transition-Metal-Catalyzed Reactions

3.2 meta- and para-C–N Bond Formation

4 C–N Cross-Dehydrogenative Coupling of Acidic C–H Bonds

5 Conclusions

 
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