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

Heng Zhang; Aiwen Lei

doi:10.1055/s-0037-1610380

Synthesis, Inhaltsverzeichnis

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

^aCollege of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. of China

,

Aiwen Lei *

^aCollege of Chemistry and Molecular Sciences, Wuhan University, Wuhan, Hubei 430072, P. R. of China

^bState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: aiwenlei@whu.edu.cn

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Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

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