CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 83-96
DOI: 10.1055/s-0037-1610380
short review
Copyright with the author

Electrochemical/Photochemical Aminations Based on Oxidative Cross-Coupling between C–H and N–H

Heng Zhang 
a   College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. of China
,
Aiwen Lei  *
a   College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. of China
b   State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China   Email: aiwenlei@whu.edu.cn
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (21390402, 21520102003, 21272180) and the Natural Science Foundation of Hubei Province (2017CFA010, 2016CFB571). The Program of Introducing Talents of Discipline to Universities of China (111 Program) is also appreciated.
Further Information

Publication History

Received: 16 October 2018

Accepted: 18 October 2018

Publication Date:
15 November 2018 (online)

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Dedicated to Professor Xiyan Lu on the occasion of his 90th birthday

Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

The construction of nitrogen-containing molecules remains at the cutting edge of organic synthesis because of its wide application in various areas. Instead of prefunctionalized substrates, using free C–H and N–H bonds in the starting materials can supply a more sustainable avenue to the C–N bond-forming reactions. Compared with the well-developed transition-metal-catalyzed protocols, the strategy of introducing optical or electrical energy into reactions is fantastic and appealing. As a result, visible light or electricity mediated amination transformations have continued to develop over the past several years. In this short review, recent progress of carbon–nitrogen bond-forming reactions based on the oxidative cross coupling between C(sp2, sp3)–H and N–H are summarized.

1 Introduction

2 C(sp2)–H/N–H Oxidative Cross Coupling

2.1 Aryl C(sp2)–H as C Nucleophiles

2.1.1 Azoles as N Nucleophiles

2.1.2 Sulfonamides or Sulfonimides as N Nucleophiles

2.1.3 NH3 as N Nucleophile

2.1.4 Morpholine as N Nucleophile

2.1.5 Diaryl Amines as N Nucleophiles

2.1.6 Primary Amines as N Nucleophiles

2.1.7 Imides as N Nucleophiles

2.1.8 Imines as N Nucleophiles

2.2 Alkenyl C(sp2)–H as C Nucleophiles

2.3 Aldehydic C(sp2)–H as C Nucleophiles

3 C(sp3)–H/N–H Oxidative Cross Coupling

3.1 Benzylic C(sp3)–H as C Nucleophiles

3.2 α-C(sp3)–H as C Nucleophiles

4 Conclusions and Outlook

Key words

oxidative cross coupling - amination - C–H bond functionalization - electrochemistry - photochemistry
 

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