溴二氟甲基三甲基硅烷的合成及其在有机合成中的应用

doi:10.6023/cjoc202306024

有机化学 ›› 2023, Vol. 43 ›› Issue (10): 3491-3507.DOI: 10.6023/cjoc202306024 上一篇下一篇

所属专题：有机氟化学虚拟合辑；有机硅化学专辑-2023

综述与进展

溴二氟甲基三甲基硅烷的合成及其在有机合成中的应用

涂志^a, 余金生^a^,^*(), 周剑^a^,^b^,^c

a 华东师范大学化学与分子工程学院上海分子治疗与新药创制工程技术研究中心上海市绿色化学与化工过程绿色化重点实验室上海 200062
b 中国科学院上海有机化学研究所金属有机化学国家重点实验室上海 200032
c 海南师范大学热带药用资源化学教育部重点实验室海口 571127

收稿日期:2023-06-27 修回日期:2023-08-23 发布日期:2023-08-30
基金资助:
国家自然科学基金(22171087); 国家自然科学基金(21971067); 上海市教育委员会科研创新计划(2023ZKZD37); 上海市科技创新行动计划(21N41900500); 上海市科技创新行动计划(20JC1416900)

Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis

Zhi Tu^a, Jinsheng Yu^a(), Jian Zhou^a^,^b^,^c

a Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Hainan Normal University, Haikou 571127

Received:2023-06-27 Revised:2023-08-23 Published:2023-08-30
Contact: *E-mail: jsyu@chem.ecnu.edu.cn
Supported by:
National Natural Science Foundation of China(22171087); National Natural Science Foundation of China(21971067); Innovation Program of Shanghai Municipal Education Commission(2023ZKZD37); Shanghai Science and Technology Innovation Action Plan(21N41900500); Shanghai Science and Technology Innovation Action Plan(20JC1416900)

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摘要/Abstract

溴二氟甲基三甲基硅烷(TMSCF₂Br)自2011年首次被作为二氟卡宾前体报道以来, 已发展成为一种重要的二氟甲(烷)基化试剂, 并在有机合成中得到了广泛应用. 在简要介绍TMSCF₂Br合成方法的基础上, 重点阐述了利用TMSCF₂Br作为二氟卡宾前体或三甲基硅基二氟甲基自由基前体实现不同底物的系列二氟甲基或氟烷基化反应的研究进展. 藉此对TMSCF₂Br在有机合成反应的活化方式和机理及其应用优势与不足等进行分析讨论, 为从事有机合成和有机氟化学相关的科研人员提供一些参考与启发.

关键词: 溴二氟甲基三甲基硅烷, 二氟卡宾, 三甲基硅基二氟甲基自由基, 二氟甲基化, 二氟烷基化

Bromodifluoromethyl trimethylsilane (TMSCF₂Br) has proved to be an important difluoromethyl(alkyl)ation reagent that is widely applied in organic synthesis over the past decade, since it was used as a difluorocarbene precursor in 2011. This review aims to provide a briefly summary for the synthesis of TMSCF₂Br, and to introduce the recent advances in the applications of TMSCF₂Br as a difluorocarbene or trimethylsilyldifluoromethyl radical precursor for developing various difluoromethyl(alkyl)ations of different kinds of substrates. Meanwhile, the activation ways of TMSCF₂Br and the possible mechanism, as well as its advantages and disadvantages in each kind of reactions are detailedly disccussed, which might provide some references and inspiration for researchers engaged in organic synthesis and organic fluorine chemistry.

Key words: (bromodifluoromethyl)trimethylsilane, difluorocarbene, trimethylsilyldifluoromethyl radical, difluoromethylation, difluoroalkylation

引用此文

涂志, 余金生, 周剑. 溴二氟甲基三甲基硅烷的合成及其在有机合成中的应用[J]. 有机化学, 2023, 43(10): 3491-3507.

Zhi Tu, Jinsheng Yu, Jian Zhou. Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis[J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3491-3507.

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图/表 43

图式1. TMSCF2Br的合成方法

Scheme 1. Synthetic methods toward TMSCF2Br

图式2. TMSCF2Br作为二氟卡宾前体试剂的首次应用

Scheme 2. First application of TMSCF2Br as a difluocarbene precursor

图式3. 醛的亲核溴或碘二氟甲基化反应

Scheme 3. Nucleophilic bromo- or iododifluoromethylation of aldehydes

图式4. TMSCF2Br与K-dtc和醛的三组分反应

Scheme 4. Three-component reaction of K-dtc, aldehydes and TMSCF2Br

图式5. TMSCF2Br与醛的亲核苯亚磺酰(芳基硫)二氟甲基化反应

Scheme 5. Nucleophilic phenylsulfonyl(arylthio)difluorometh- ylation of aldehydes with TMSCF2Br

图式6. 利用TMSCF2Br实现醛类化合物的氟化-氨基羰基化反应

Scheme 6. TMSCF2Br-enabled fluorination-aminocarbonylation of aldehydes

图式7. 利用TMSCF2Br实现醛C—H键可控单和双二氟亚甲基插入反应

Scheme 7. Controllable single and double difluoromethylene formal insertions into C—H bonds of aldehydes with TMSCF2Br

图式8. 亚胺的亲核溴二氟甲基化反应

Scheme 8. Nucleophile bromodifluoromethylation of imines

图式9. 酮/硝基烯烃与TMSCF2Br亲核二氟甲基化反应

Scheme 9. Nucleophilic difluoromethylation of ketones or nitroolefins with TMSCF2Br

图式10. 利用TMSCF2Br实现吡啶氮氧化物C2位亲核二氟甲基化反应

Scheme 10. C2-position nucleophilic difluoromethylation of pyridine N-oxides with TMSCF2Br

图式11. 羧酸的选择性单/双二氟甲基化反应

Scheme 11. Selective single or bis-difluoromethylation of carboxylic acids

图式12. 溴二氟甲基化硒化物的合成

Scheme 12. Synthesis of bromodifluoromethylated selenide

图式13. 酮与TMSCF2Br的二氟同系化反应

Scheme 13. Difluorohomologation of ketones with TMSCF2Br

图式14. 酮与TMSCF2Br的单氟同系化反应

Scheme 14. Monofluorohomologation of ketones with TMS- CF2Br

图式15. 利用TMSCF2Br实现从酮35合成二氟环戊烯酮

Scheme 15. Synthesis of difluorocyclopentenones from ketone 35 using TMSCF2Br.

图式16. 四取代溴氟烯烃的合成

Scheme 16. Synthesis of tetrasubstituted bromofluoroolefins

图式17. KOH促进TMSCF2Br与(硫)醇的二氟甲基化反应

Scheme 17. KOH promotes the difluoromethylation reaction of TMSCF2Br with (thio)alcohols

图式18. TMSCF2Br与烷基醇的二氟甲基化反应

Scheme 18. Difluoromethylation of alkyl alcohols with TMS- CF2Br.

图式19. S-二氟甲基二硫代氨基甲酸酯的合成

Scheme 19. Synthesis of S-difluoromethyl dithiocarbamate.

图式20. 羧酸与TMSCF2Br的二氟甲基化反应

Scheme 20. Difluoromethylation of carboxylic acids with TMS- CF2Br

图式21. TMSCF2Br参与的环(硫)醚的开环反应

Scheme 21. Ring-opening of cyclo(sulfide) ethers with TMS- CF2Br

图式22. TMSCF2Br实现的氮和磷亲核试剂的二氟甲基化反应

Scheme 22. Difluoromethylation of N- or P-nucleophiles with TMSCF2Br

图式23. 酮腙与TMSCF2Br的N-二氟甲基化反应

Scheme 23. N-Difluoromethylation of ketone hydrazones with TMSCF2Br

图式24. TMSCF2Br介导的非张力环胺的开环反应

Scheme 24. Ring-opening of non-tensile cyclic amines with TMSCF2Br

图式25. TMSCF2Br与叔胺和CO2的三组分反应

Scheme 25. Three-component reaction of tertiary amine and CO2 with TMSCF2Br

图式26. TMSCF2Br与2-吡啶酮的选择性二氟甲基化反应

Scheme 26. Selective difluoromethylation of 2?pyridones with TMSCF2Br

图式27. 伯胺与TMSCF2Br反应合成二氟甲基甲酰亚胺类化合物

Scheme 27. Synthesis of difluoromethylated formimidamide from primary amine and TMSCF2Br

图式28. TMSCF2Br与叔膦合成五配位膦烷

Scheme 28. Synthesis of pentacoordinate phosphoranes from tertiary phosphines and TMSCF2Br

图式29. 有机锌试剂与TMSCF2Br的二氟甲基化反应

Scheme 29. Difluoromethylation of organozinc reagent with TMSCF2Br

图式30. TMSCF2Br与β-酮酸酯(酰胺)的C-选择性二氟甲基化反应

Scheme 30. C-selective difluoromethylation of β-ketoesters or β-ketoamides with TMSCF2Br

图式31. β-酮酸酯与TMSCF2Br的不对称二氟甲基化反应

Scheme 31. Asymmetric difluoromethylation of β-ketoesters with TMSCF2Br

图式32. sp3-或sp-杂化碳亲核试剂与TMSCF2Br的二氟甲基化反应

Scheme 32. Difluoromethylation of sp3- or sp-hybrided C-nuc- leophiles with TMSCF2Br

图式33. 胡金波等发展的重氮与TMSCF2Br的偕二氟烯基化反应

Scheme 33. Gem-difluoroolefination of diazo compounds with TMSCF2Br by Hu et al.

图式34. 王剑波等发展的重氮与TMSCF2Br的偕二氟烯基化反应

Scheme 34. Gem-difluoroolefination of diazo compounds with TMSCF2Br by Wang et al.

图式35. TMSCF2Br与金属络合物的反应

Scheme 35. Reaction of metal complex with TMSCF2Br

图式36. 三氟甲基砜与TMSCF2Br的偕二氟烯基化反应

Scheme 36. Gem-difluoroolefination of trifluoromethyl sulfones with TMSCF2Br

图式37. TMSCF2Br与异氰和亚胺或烯烃或炔烃的三组分反应

Scheme 37. Three-component reaction of TMSCF2Br and isocyanide with imine or olefins or alkynes

图式38. 铜介导芳基碘化物与TMSCF2H和TMSCF2Br的四氟乙基化和六氟丙基化

Scheme 38. Copper-mediated tetrafluoroethylation and hexafluoropropylation of aryl iodides and TMSCF2H with TMS- CF2Br

图式39. 缺电子烯烃与TMSCF2Br的自由基二氟烷基化反应

Scheme 39. Radical difluoroalkylation of electron-deficient alkenes with TMSCF2Br

图式40. 光氧化还原催化烯醇硅醚与TMSCF2Br的二氟烷基化反应

Scheme 40. Photoredox-catalyzed difluoroalkylation of silyl enol ethers with TMSCF2Br

图式41. 铁催化TMSCF2Br参与的多组分偶联反应

Scheme 41. Iron-catalyzed multicomponent coupling involving TMSCF2Br

图式42. TMSCF2Br与脱氢丙氨酸衍生物的还原氢二氟烷基化反应

Scheme 42. Reductive hydrodifluoroalkylation of dehydroalanine derivatives with TMSCF2Br

图式43. 钴催化TMSCF2Br与格式试剂ArMgBr的偶联反应

Scheme 43. Cobalt-catalyzed coupling of TMSCF2Br with Ar- MgBr

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溴二氟甲基三甲基硅烷的合成及其在有机合成中的应用

Synthesis of (Bromodifluoromethyl)trimethylsilane and Its Applications in Organic Synthesis

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