Direct Reductive Coupling of Nitro Compounds for the Synthesis of Advanced Amines

Tao Li; Albert S. C. Chan; Shan-Shui Meng

doi:10.1055/s-0042-1751503

Synthesis, Table of Contents

Synthesis 2024; 56(05): 733-750
DOI: 10.1055/s-0042-1751503

short review

Direct Reductive Coupling of Nitro Compounds for the Synthesis of Advanced Amines

Tao Li

^aChongqing Institute of Green and Intelligent Technology, Chongqing School, University of Chinese Academy of Sciences (UCAS Chongqing), Chongqing, 400714, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

,

Albert S. C. Chan∗

^aChongqing Institute of Green and Intelligent Technology, Chongqing School, University of Chinese Academy of Sciences (UCAS Chongqing), Chongqing, 400714, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing, 100049, P. R. of China

^cSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, P. R. of China

,

Shan-Shui Meng∗

^cSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, P. R. of China

› Author Affiliations

Abstract

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Dedicated to the 20th anniversary of the School of Pharmaceutical Sciences, Sun Yat-sen University.

Abstract

Direct reductive coupling of nitro compounds with C-coupling partners is an atom- and step-economical strategy to access polyfunctional advanced amines. Due to the extremely complex process involved in the reduction of nitro compounds and the high reactivity of N,O-intermediates, few reliable methodologies have been reported for the reductive coupling of nitro compounds since the initial studies. To address this significant challenge, numerous endeavors have been devoted to this important area over the past hundred years. In this short review, we summarize recent advances in this domain and discuss the mechanisms of these appealing reductive coupling transformations.

1 Introduction

2 Reductive Coupling of Nitro Compounds with Organometallic Reagents

3 Reductive Coupling of Nitro Compounds with Arylboronic Acids

4 Reductive Coupling of Nitro Compounds with Alkenes

5 Reductive Coupling of Nitro Compounds with Alkyl/Aryl Halides

6 Reductive Coupling of Nitro Compounds with Alcohols and Their Derivatives

7 Conclusion

Key words

reductive coupling - nitro compounds - advanced amines - organometallic reagents - boronic acids - alkenes - alkyl/aryl halides - alcohols

Full Text

References

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