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Synthesis 2020; 52(06): 796-806
DOI: 10.1055/s-0039-1690789
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Radical Nitration Using tert-Butyl Nitrite

Si-Zhe Song
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Youren Dong∗
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Guo-Ping Ge∗
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Qiang Li
b   Institution of Functional Organic Molecules and Materials, School of Chemistry and Chemical Engineering, Liaocheng University, Liaocheng 252059, P. R. of China
,
Wen-Ting Wei∗
a   State Key Laboratory Base of Novel Functional Materials and Preparation Science, State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
› Author AffiliationsThis work is sponsored by the National Natural Science Foundation of China (Grant No. 21801142), the Natural Science Foundation of Zhejiang Province (No. LQ18B020002), the Natural Science Foundation of the Ningbo Municipal Natural Science Foundation (No. 2018A610412; No. 2019A610021) and the K. C. Wong Magna Fund in Ningbo University.
Further Information

Publication History

Received: 08 November 2019

Accepted after revision: 10 December 2019

Publication Date:
08 January 2020 (online)

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Abstract

Nitro compounds serve as valuable intermediates for pharmaceuticals, agrochemicals, dyes, and polymers. In recent years, radical nitration using tert-butyl nitrite (t-BuONO) has attracted wide attention and desirable progress has been made. On the one hand, t-BuONO is a potential active nitro radical source and can react with various functional groups. On the other hand, as a green and novel nitration reagent, t-BuONO has relatively low price and can easily produce a radical under mild conditions, which undoubtedly provides a simple and efficient way for nitration reactions. To date, some important reviews are available that summarize the synthesis of nitro compounds. To the best of our knowledge, however, there is still no review that exclusively discusses the synthesis of nitro compounds using t-BuONO through a radical strategy. Therefore, this review aims to highlight the recent advances in radical nitration using t-BuONO as nitration reagent. The main progress in this area has been presented according to the type of reaction substrates. Special attention has been paid discussion of the reaction mechanisms and selected examples of substrates have been given. We hope this paper will be a useful reference and inspiration for those who are exploring the synthesis of nitro compounds using t-BuONO.

1 Introduction

2 Radical Nitration of Alkenes

3 Radical Nitration of Aromatics

4 Radical Nitration of Alkynes

5 Radical Nitration of 1,n-Enynes

6 Radical Nitration of Alkanes

7 Summary and Perspective

Key words

nitration - tert-butyl nitrite - radical reaction - C–N bond