二氟甲基重氮甲烷作为含氟砌块的应用研究进展

doi:10.6023/cjoc202009055

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1275-1287.DOI: 10.6023/cjoc202009055 上一篇下一篇

综述与进展

二氟甲基重氮甲烷作为含氟砌块的应用研究进展

朱文庆^a, 许婷怡^a, 韩文勇^b^,^c^,^*()

a 西安工程大学环境与化学工程学院西安 710048
b 遵义医科大学药学院贵州省生物催化与手性药物合成重点实验室贵州遵义 563006
c 遵义医科大学基础药理教育部重点实验室暨特色民族药教育部国际合作联合实验室贵州遵义 563006

收稿日期:2020-09-28 修回日期:2020-11-02 发布日期:2020-12-01
通讯作者: 韩文勇
基金资助:
国家自然科学基金(21762054); 遵义医科大学优秀青年人才支持计划(18ZY-002)

Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

Wenqing Zhu^a, Tingyi Xu^a, Wenyong Han^b^,^c^,^*()

a School of Environmental and Chemical Engineering, Xi?an Polytechnic University, Xi?an 710048
b Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, Guizhou 563006
c Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi, Guizhou 563006

Received:2020-09-28 Revised:2020-11-02 Published:2020-12-01
Contact: Wenyong Han
About author:
* Corresponding authors. E-mail: hanwy@zmu.edu.cn; hanwy@126.com
Supported by:
National Natural Science Foundation of China(21762054); Outstanding Youth Talent Support Programs from Zunyi Medical University(18ZY-002)

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摘要/Abstract

二氟甲基化反应经过近二十年的发展已取得了较为显著的研究成果. 除直接和间接二氟甲基化反应外, 二氟甲基砌块参与的化学转化是一种向有机化合物中引入二氟甲基的新策略. 相比于亲电、亲核和自由基二氟甲基化试剂, 二氟甲基砌块的种类仍然有限并有待进一步开发. 其中, 二氟甲基重氮甲烷是近年来发展的一类新型含氟砌块, 受到了研究学者们的高度关注. 综述了二氟甲基重氮甲烷及其稳定替代物的最新应用研究进展, 着重介绍了其反应类型及相关机理, 并对今后的发展方向进行了展望.

关键词: 二氟甲基重氮甲烷, 二氟甲基化, 含氟砌块, 吡唑

Difluoromethylation has achieved remarkable progress in the past two decades. In addition to the direct difluoromethylation and the stepwise difluoromethylation, chemical transformation starting from CF₂H-containing building blocks is a novel strategy to introduce difluoromethyl group into organic compounds. Compared with electrophilic-, nucleo- philic- and free radical-difluoromethylation reagents, the types of CF₂H-containing building blocks are still limited and less explored. Among them, difluoromethyl diazomethane (CF₂HCHN₂) is a new type of fluorine-containing building block developed in recent years, which has received much attention from researchers. The recent progress in the application of difluoromethyl diazomethane and its surrogates as fluorine-containing building blocks is summarized, focusing on the reaction types and related mechanisms, and the developmental direction in the future is prospected.

Key words: difluoromethyl diazomethane, difluoromethylation, fluorinated building block, pyrazole

引用此文

朱文庆, 许婷怡, 韩文勇. 二氟甲基重氮甲烷作为含氟砌块的应用研究进展[J]. 有机化学, 2021, 41(4): 1275-1287.

Wenqing Zhu, Tingyi Xu, Wenyong Han. Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1275-1287.

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图/表 22

图1. 含有二氟甲基的药物和生物活性分子

Figure 1. Difluoromethyl-containing drugs and bioactive molecules

图式1. 三氟甲基重氮甲烷(2)和二氟甲基重氮甲烷(4)的制备及其性质

Scheme 1. Preparations of CF3CHN2 (2) and CF2HCHN2 (4) as well as their properties

图式2. 二氟甲基重氮甲烷与缺电子炔烃的[3+2]环加成反应

Scheme 2. [3+2] Cycloaddition reaction of CF2HCHN2 with electron-deficient alkynes

图式3. 二氟甲基重氮甲烷与缺电子烯烃的[3+2]环加成反应

Scheme 3. [3+2] cycloaddition reaction of CF2HCHN2 with electron-deficient alkenes

图式4. 利用二氟甲基重氮甲烷合成N-亚硝基二氟甲基吡唑啉类化合物

Scheme 4. Synthesis of N-nitroso CF2H-pyrazolines with CF2HCHN2

图式5. 利用二氟甲基重氮甲烷合成4-氟-6-二氟甲基哒嗪

Scheme 5. Synthesis of 4-fluoro-6-(difluoromethyl)pyridazine with CF2HCHN2

图式6. 二氟甲基重氮甲烷在含氮杂环化合物合成中的应用

Scheme 6. Application of CF2HCHN2 in the synthesis of N-heterocyclics

图式7. 不期望的三组分反应以及二氟甲基吡唑类化合物的合成设计

Scheme 7. Unexpected three-component reaction as well as synthetic design of CF2H-containing pyrazoles

图式8. 利用二氟甲基重氮甲烷合成二氟甲基取代异噁唑类化合物

Scheme 8. Synthesis of difluoromethyl substituted isoxazole compounds with CF2HCHN2

图式9. 铜催化四组分反应合成N-二氟乙基酰亚胺类化合物

Scheme 9. Copper-catalyzed four-component reaction for the synthesis of N-difluoroethyl imides

图2. 含N-二氟乙基酰亚胺的药物分子类似物

Figure 2. Analogues of drug molecular containing N-difluoro- ethyl imides

图式10. 二氟甲基重氮甲烷与羧酸的酯化反应

Scheme 10. Esterification of CF2HCHN2 with carboxylic acids

图3. 市售药物和天然产物的二氟乙酯类似物

Figure 3. Difluoroethyl ester analogues of marketed drugs and natural products

图式11. 二氟甲基重氮甲烷的偕双官能团化反应

Scheme 11. gem-Difunctionalization of CF2HCHN2

图式12. 连续流反应合成二氟甲基取代的吡唑啉和吡唑类化合物

Scheme 12. Synthesis of CF2H-containing pyrazolines and pyra- zoles by continuous flow reaction

图式13. 连续流反应合成二氟甲基取代环丙烷

Scheme 13. Synthesis of difluoromethyl substituted cyclopropane by continuous flow reaction

图式14. 采用连续流反应器的二氟甲基重氮甲烷的[3+2]环加成反应

Scheme 14. [3+2] cycloaddition reaction of CF2HCHN2 using continuous flow reactors

图式15. 多步连续流动合成含氟吡唑类和吡唑啉类化合物

Scheme 15. Multi-step continuous flow synthesis of fluorinated pyrazoles and pyrazolines

图4. 基于连续流模块合成的含二氟甲基农药分子

Figure 4. CF2H-containing pesticides synthesized by continuous flow modules

图式16. Ph2S+CH2CF2H–OTf作为二氟甲基重氮甲烷替代物参与的反应

Scheme 16. Reactions of Ph2S+CH2CF2H–OTf as the surrogate of CF2HCHN2

图式17. Ps-DFA作为二氟甲基重氮甲烷替代物参与的反应

Scheme 17. Reactions of Ps-DFA as the surrogate of CF2HCHN2

图式18. DFHZ-Tfs作为二氟甲基重氮甲烷替代物参与的反应

Scheme 18. Reactions of DFHZ-Tfs as the surrogate of CF2HCHN2

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二氟甲基重氮甲烷作为含氟砌块的应用研究进展

Recent Progress in the Application of Difluoromethyl Diazomethane as Fluorine-Containing Building Block

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