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

Author:

Zhang Heng1ORCID,Lei Aiwen12ORCID

Affiliation:

1. College of Chemistry and Molecular Sciences, Wuhan University

2. State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University

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 Introduction2 C(sp2)–H/N–H Oxidative Cross Coupling2.1 Aryl C(sp2)–H as C Nucleophiles2.1.1 Azoles as N Nucleophiles2.1.2 Sulfonamides or Sulfonimides as N Nucleophiles2.1.3 NH3 as N Nucleophile2.1.4 Morpholine as N Nucleophile2.1.5 Diaryl Amines as N Nucleophiles2.1.6 Primary Amines as N Nucleophiles2.1.7 Imides as N Nucleophiles2.1.8 Imines as N Nucleophiles2.2 Alkenyl C(sp2)–H as C Nucleophiles2.3 Aldehydic C(sp2)–H as C Nucleophiles3 C(sp3)–H/N–H Oxidative Cross Coupling3.1 Benzylic C(sp3)–H as C Nucleophiles3.2 α-C(sp3)–H as C Nucleophiles4 Conclusions and Outlook

Funder

National Natural Science Foundation of China

Natural Science Foundation of Hubei Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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