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

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(sp 2 , sp 3 )-H and N-H are summarized. 1 Introduction 2 C(sp 2 )-H/N-H Oxidative Cross Coupling 2.1 Aryl C(sp 2 )-H as C Nucleophiles 2.1.1 Azoles as N Nucleophiles 2.1.2 Sulfonamides or Sulfonimides as N Nucleophiles 2.1.3 NH 3 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(sp 2 )-H as C Nucleophiles 2.3 Aldehydic C(sp 2 )-H as C Nucleophiles 3 C(sp 3 )-H/N-H Oxidative Cross Coupling 3.1 Benzylic C(sp 3 )-H as C Nucleophiles 3.2 α-C(sp 3 )-H as C Nucleophiles 4 Conclusions and Outlook.