Application of Flow Chemistry in Halogenation

doi:10.6023/cjoc202007051

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1002-1011.DOI: 10.6023/cjoc202007051 Previous Articles Next Articles

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流动化学在卤化反应中的应用

刘玎^a^,^b, 朱园园^c, 古双喜^a^,^b^,^*(), 陈芬儿^a^,^b^,^d^,^*()

a 武汉工程大学化工与制药学院绿色化工过程教育部重点实验室武汉 430205
b 武汉工程大学药物研究院武汉 430205
c 武汉工程大学化学与环境工程学院武汉 430205
d 复旦大学化学系上海 200433

收稿日期:2020-07-22 修回日期:2020-09-14 发布日期:2020-10-12
通讯作者: 古双喜, 陈芬儿
基金资助:
国家自然科学基金(21877087); 国家自然科学基金(21602164); 新型反应器与绿色化学工艺湖北省重点实验室(武汉工程大学)开放基金(K202004)

Application of Flow Chemistry in Halogenation

Ding Liu^a^,^b, Yuanyuan Zhu^c, Shuangxi Gu^a^,^b^,^*(), Fener Chen^a^,^b^,^d^,^*()

a Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering and Pharmacy,Wuhan Institute of Technology, Wuhan 430205
b Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205
c School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205
d Department of Chemistry, Fudan University, Shanghai 200433

Received:2020-07-22 Revised:2020-09-14 Published:2020-10-12
Contact: Shuangxi Gu, Fener Chen
About author:
* Corresponding authors. E-mail: shuangxigu@163.com;
rfchen@fudan.edu.cn
Supported by:
National Natural Science Foundation of China(21877087); National Natural Science Foundation of China(21602164); Open Fund of Hubei Key Laboratory of Novel Reactor and Green Chemical Technology (Wuhan Institute of Technology)(K202004)

The halogenation of organic compounds is one of the most important transformations in organic synthesis. However, there are some problems in traditional batch halogenation, such as high exothermicity, poor selectivity and the use of highly toxic and corrosive halogenating agents. Flow chemistry has its unique advantages such as high mixing efficiency, fast heat and mass transfer performance, accurate control over process parameters and enhanced process safety, reduced energy input and so on. According to the classification of halogenation of organic compounds, the main progress of flow chemistry in fluorination, chlorination, bromination and iodization is summarized systematically, and its development trend is prospected.

Key words: flow chemistry, microreactor, continuous flow, halogenation, organic synthesis

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Ding Liu, Yuanyuan Zhu, Shuangxi Gu, Fener Chen. Application of Flow Chemistry in Halogenation[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1002-1011.

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Fig. & Tab. 19

Scheme 1. Fluorination of β-dicarbonyl compounds

Scheme 2. Fluorination of 4-methoxynitrobenzene

Scheme 3. Fluorination of benzaldehyde derivatives

Scheme 4. Use of DAST in continuous flow reactors

Scheme 5. Continuous flow fluorination of substituted phenyl lithium

Scheme 6. Continuous flow chlorination of silane

Scheme 7. Synthesis of 3-chloro-N-benzyl-propanamide from acrylic acid

Scheme 8. Conversion of alcohols to chlorides using HCl gas

Scheme 9. Photochemical chlorination of hydrocarbons using in situ generated Cl2

Scheme 10. Microflow chlorination of cycloalkanes with sulfuryl chloride

Scheme 11. Bromination reaction of thiophene

Scheme 12. In situ generation of KOBr for bromination of methylsulfones and methanesulfonates

Scheme 13. Bromination of alkanes and alkylarenes

Scheme 14. Bromination reaction of 1,2,4-trifluorobenzene

Scheme 15. Bromination of enamine bromide using NBS

Scheme 16. Bromination of 5-methylpyrimidine

Scheme 17. Selective monoiodination of 1,3-dimethoxybenene in continuous flow microreactor

Scheme 18. Continuous flow iodination of indoles

Scheme 19. Iodination of organic compounds using ICl

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流动化学在卤化反应中的应用

Application of Flow Chemistry in Halogenation

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