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

doi:10.6023/cjoc202306024

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (10): 3491-3507.DOI: 10.6023/cjoc202306024 Previous Articles Next Articles

Special Issue: 有机氟化学虚拟合辑；有机硅化学专辑-2023

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)

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

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 43

Scheme 1. Synthetic methods toward TMSCF2Br

Scheme 2. First application of TMSCF2Br as a difluocarbene precursor

Scheme 3. Nucleophilic bromo- or iododifluoromethylation of aldehydes

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

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

Scheme 6. TMSCF2Br-enabled fluorination-aminocarbonylation of aldehydes

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

Scheme 8. Nucleophile bromodifluoromethylation of imines

Scheme 9. Nucleophilic difluoromethylation of ketones or nitroolefins with TMSCF2Br

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

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

Scheme 12. Synthesis of bromodifluoromethylated selenide

Scheme 13. Difluorohomologation of ketones with TMSCF2Br

Scheme 14. Monofluorohomologation of ketones with TMS- CF2Br

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

Scheme 16. Synthesis of tetrasubstituted bromofluoroolefins

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

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

Scheme 19. Synthesis of S-difluoromethyl dithiocarbamate.

Scheme 20. Difluoromethylation of carboxylic acids with TMS- CF2Br

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

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

Scheme 23. N-Difluoromethylation of ketone hydrazones with TMSCF2Br

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

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

Scheme 26. Selective difluoromethylation of 2?pyridones with TMSCF2Br

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

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

Scheme 29. Difluoromethylation of organozinc reagent with TMSCF2Br

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

Scheme 31. Asymmetric difluoromethylation of β-ketoesters with TMSCF2Br

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

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

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

Scheme 35. Reaction of metal complex with TMSCF2Br

Scheme 36. Gem-difluoroolefination of trifluoromethyl sulfones with TMSCF2Br

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

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

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

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

Scheme 41. Iron-catalyzed multicomponent coupling involving TMSCF2Br

Scheme 42. Reductive hydrodifluoroalkylation of dehydroalanine derivatives with TMSCF2Br

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

References 49

[1]	(a) Uneyama K. Organofluorine Chemistry, Blackwell, Oxford, 2006.
	(b) Chambers R. D. Fluorine in Organic Chemistry, Blackwell, Oxford, 2004.
	(c) Kirsch P. Modern Fluoroorganic Chemistry: Synthesis Reactivity, Applications, 2nd ed., Wiley-VCH, Weinheim, 2013.
[2]	(a) Erickson J. A.; McLoughlin J. I. J. Org. Chem. 1995, 60, 1626. doi: 10.1021/jo00111a021 pmid: 32027173
	(b) Sap J. B.; Meyer C. F.; Straathof N. J.; Iwumene N.; Am Ende C. W.; Trabanco A. A.; Gouverneur V. J. Am. Chem. Soc. 2017, 139, 9325. doi: 10.1021/jacs.7b04457 pmid: 32027173
	(c) Zafrani Y.; Saphier S.; Gershonov E. Future Med. Chem. 2020, 12, 361. doi: 10.4155/fmc-2019-0309 pmid: 32027173
	(d) Sap J. B.; Meyer C. F; Straathof N. J.; Iwumene N.; Am Ende C. W.; Trabanco A. A.; Gouverneur V. Chem. Soc. Rev. 2021, 50, 8214. doi: 10.1039/D1CS00360G pmid: 32027173
[3]	(a) Prakash G. K. S.; Yudin A. K. Chem. Rev. 1997, 97, 757. pmid: 11848888
	(b) Liu X.; Xu C.; Wang M.; Liu Q. Chem. Rev. 2015, 115, 683. doi: 10.1021/cr400473a pmid: 11848888
	(c) Dilman A. D.; Levin V. V. Mendeleev Commun. 2015, 25, 239. doi: 10.1016/j.mencom.2015.07.001 pmid: 11848888
	(d) Rong J.; Ni C.-F.; Hu J.-B. Asian J. Org. Chem. 2017, 6, 139. doi: 10.1002/ajoc.v6.2 pmid: 11848888
	(e) Chen D.-B.; Gao X.; Song S.-R.; Kou M.; Ni C.-F.; Hu J.-B. Sci. Sin.: Chim. 2023, 53, 375. pmid: 11848888
[4]	Wang F.; Zhang W.; Zhu J.-M.; Li H.-F.; Huang K.-W.; Hu J.-B. Chem. Commun. 2011, 47, 2411 doi: 10.1039/C0CC04548A
[5]	Li L.-C.; Wang F.; Ni C.-F.; Hu J.-B. Angew. Chem., Int. Ed. 2013, 52, 12390. doi: 10.1002/anie.v52.47
[6]	(a) Hu J.-B.; Zhang W.; Wang F. Chem. Commun. 2009, 7465. pmid: 28051859
	(b) Hu J.-B. J. Fluorine Chem. 2009, 130, 1130. doi: 10.1016/j.jfluchem.2009.05.016 pmid: 28051859
	(c) Qing F.-L.; Zheng F. Synlett 2011, 2011, 1052. doi: 10.1055/s-0030-1259947 pmid: 28051859
	(d) Meanwell N. A. J. Med. Chem. 2011, 54, 2529. doi: 10.1021/jm1013693 pmid: 28051859
	(e) Ni C.-F.; Hu J.-B. Synthesis 2014, 46, 842. doi: 10.1055/s-00000084 pmid: 28051859
	(f) Belhomme M. C.; Besset T.; Poisson T.; Pannecoucke X. Chem.-Eur. J. 2015, 21, 12836. doi: 10.1002/chem.v21.37 pmid: 28051859
	(g) Zafrani Y.; Yeffet D.; Sod-Moriah G.; Berliner A.; Amir D.; Marciano D.; Gershonov E.; Saphier S. J. Med. Chem. 2017, 60, 797. doi: 10.1021/acs.jmedchem.6b01691 pmid: 28051859
[7]	(a) Wang J.; Sánchez-Roselló M.; Aceña J. L.; Del Pozo C.; Srochinsky A. E.; Fustero S.; Soloshonok V. A.; Liu H. Chem. Rev. 2014, 114, 2432. doi: 10.1021/cr4002879 pmid: 19296694
	(b) Chowdhury M. A.; Abdellatif K. R.; Dong Y.; Das D.; Suresh M. R.; Knaus E. E. J. Med. Chem. 2009, 52, 1525. doi: 10.1021/jm8015188 pmid: 19296694
	(c) Gewehr M.; Gladwin R. J.; Brahm L. US 2012/0245031, 2012. pmid: 19296694
	(d) Pérez R. A.; Sánchez-Brunete C.; Miguel E.; Tadeo J. L. J. Agric. Food Chem. 1998, 46, 1864. doi: 10.1021/jf970854b pmid: 19296694
[8]	(a) Wang X.; Pan S.-T.; Luo Q.-Y.; Wang Q.; Ni C.-F.; Hu J.-B. J. Am. Chem. Soc. 2022, 144, 12202. doi: 10.1021/jacs.2c03104 pmid: 35786906
	(b) Trang B.; Li Y.-L.; Xue X.-S.; Ateia M.; Houk K. N.; Dichtel W. R. Science 2022, 377, 839. doi: 10.1126/science.abm8868 pmid: 35786906
	(c) Tsyrulnikova A. S.; Vershilov S. V.; Popova L. M.; Lebedev N. V.; Litvinenko E. V.; Ismagilov N. G. J. Fluorine Chem. 2022, 257, 109972. pmid: 35786906
[9]	Evich M. G.; Davis M. J. B.; McCord J. P.; Acrey B.; Awkerman J. A.; Knappe D. R. U.; Lindstrom A. B.; Speth T. F.; Tebes-Stevens C.; Strynar M. J.; Wang Z.-Y.; Weber E. J.; Henderson W. M.; Washington J. W. Science 2022, 375, eabg9065.
[10]	(a) Krishnamoorthy S.; Prakash G. K. S. Synthesis 2017, 49, 3394. doi: 10.1055/s-0036-1588489
	(b) Yerien D. E.; Barata-Vallejo S.; Postigo A. Chem. Eur. J. 2017, 23, 14676. doi: 10.1002/chem.v23.59
	(c) Sap J. B.; Meyer C. F.; Straathof N. J.; Iwumene N.; Am Ende C. W.; Trabanco A. A.; Gouverneur V. Chem. Soc. Rev. 2021, 50, 8214. doi: 10.1039/D1CS00360G
	(d) Dilman A. D.; Levin V. V. Acc. Chem. Res. 2018, 51, 1272. doi: 10.1021/acs.accounts.8b00079
[11]	(a) Broicher V.; Geffken D. J. Organomet. Chem. 1990, 381, 315. doi: 10.1016/0022-328X(90)80061-4
	(b) Ruppert I.; Schlich K.; Volbach W. Tetrahedron Lett. 1984, 25, 2195. doi: 10.1016/S0040-4039(01)80208-2
	(c) Yudin A. K.; Prakash G. K. S.; Deffieux D.; Bradley M.; Bau R.; Olah G. A. J. Am. Chem. Soc. 1997, 119, 1572. doi: 10.1021/ja962990n
[12]	Kosobokov M. D.; Dilman A. D.; Levin V. V.; Struchkova M. I. J. Org. Chem. 2012, 77, 5850. doi: 10.1021/jo301094b pmid: 22708637
[13]	(a) Kosobokov M. D.; Levin V. V.; Struchkova M. I.; Dilman A. D. Org. Lett. 2014, 16, 3784. doi: 10.1021/ol501674n pmid: 24968144
	(b) Levin V. V.; Smirnov V. O.; Struchkova M. I.; Dilman A. D. J. Org. Chem. 2015, 80, 9349. doi: 10.1021/acs.joc.5b01590 pmid: 24968144
[14]	Maslov A. S.; Smirnov V. O.; Struchkova M. I.; Arkhipov D. E.; Dilman A. D. Tetrahedron Lett. 2015, 56, 5048. doi: 10.1016/j.tetlet.2015.07.018
[15]	Xie Q.-Q.; Zhu Z.-Y.; Ni C.-F.; Hu J.-B. Org. Lett. 2019, 21, 9138. doi: 10.1021/acs.orglett.9b03520
[16]	Liu A.; Ni C.-F.; Xie Q.-Q.; Hu J.-B. Angew. Chem., Int. Ed. 2022, 61, e202115467.
[17]	Liu A.; Ni C.-F.; Xie Q.-Q.; Hu J.-B. Angew. Chem., Int. Ed. 2023, 62, e202217088.
[18]	Tsymbal A. V.; Kosobokov M. D.; Levin V. V.; Struchkova M. I.; Dilman A. D. J. Org. Chem. 2014, 79, 7831. doi: 10.1021/jo501644m pmid: 25116859
[19]	Trifonov A. L.; Zemtsov A. A.; Levin V. V.; Struchkova M. I.; Dilman A. D. Org. Lett. 2016, 18, 3458. doi: 10.1021/acs.orglett.6b01641 pmid: 27336618
[20]	Trifonov A. L.; Dilman A. D. Org. Lett. 2021, 23, 6977 doi: 10.1021/acs.orglett.1c02603
[21]	Trifonov A. L.; Levin V. V.; Struchkova M. I.; Dilman A. D. Org. Lett. 2017, 19, 5304. doi: 10.1021/acs.orglett.7b02601 pmid: 28915059
[22]	(a) Glenadel Q.; Ismalaj E.; Billard T. J. Org. Chem. 2016, 81, 8268. doi: 10.1021/acs.joc.6b01344 pmid: 34823360
	(b) Fang Y.; Li X.; Liu C.-Y.; Tang J.; Chen Z.-P. J. Org. Chem. 2021, 86, 18081. doi: 10.1021/acs.joc.1c02349 pmid: 34823360
[23]	(a) Kosobokov M. D.; Levin V. V.; Struchkova M. I.; Dilman A. D. Org. Lett. 2015, 17, 760. doi: 10.1021/acs.orglett.5b00097 pmid: 25965426
	(b) Fedorov O. V.; Kosobokov M. D.; Levin V. V.; Struchkova M. I.; Dilman A. D. J. Org. Chem. 2015, 80, 5870. doi: 10.1021/acs.joc.5b00904 pmid: 25965426
[24]	(a) Song X.-N.; Chang J.; Zhu D.-S.; Li J.-H.; Xu C.; Liu Q.; Wang M. Org. Lett. 2015, 17, 1712. doi: 10.1021/acs.orglett.5b00488
	(b) Chang J.; Song X.-N.; Huang W.-Q.; Zhu D.-S.; Wang M. Chem. Commun. 2015, 51, 15362. doi: 10.1039/C5CC06825H
[25]	(a) Song X.-N.; Tian S.-Q.; Zhao Z.-M.; Zhu D.-S.; Wang M. Org. Lett. 2016, 18, 3414. doi: 10.1021/acs.orglett.6b01567 pmid: 28332846
	(b) Chang J.; Xu C.; Gao J.; Gao F.-Y.; Zhu D.-S.; Wang M. Org. Lett. 2017, 19, 1850. doi: 10.1021/acs.orglett.7b00611 pmid: 28332846
[26]	Zhu J.; Xu M.-H.; Gong B.-H.; Lin A.-J.; Gao S. Org. Lett. 2023, 25, 3271. doi: 10.1021/acs.orglett.3c01007
[27]	(a) Xie Q.-Q.; Ni C.-F.; Zhang R.-Y.; Li L.-C.; Rong J.; Hu J.-B. Angew. Chem., Int. Ed. 2017, 56, 3206. doi: 10.1002/anie.v56.12
	(b) Zhang R.-Y.; Ni C.-F.; Xie Q.-Q.; Hu J.-B. Tetrahedron 2020, 76, 131676. doi: 10.1016/j.tet.2020.131676
[28]	Smirnov V. O.; Maslov A. S.; Struchkova M. I.; Arkhipov D. E.; Dilman A. D. Mendeleev Commun. 2015, 25, 452. doi: 10.1016/j.mencom.2015.11.018
[29]	Krishnamurti V.; Barrett C.; Ispizua-Rodriguez X.; Coe M.; Prakash G. K. S. Org. Lett. 2019, 21, 9377. doi: 10.1021/acs.orglett.9b03604 pmid: 31742416
[30]	(a) Zhang R.-Y.; Li Q.-G.; Ni C.-F.; Hu J.-B. Chem. Eur. J. 2021, 27, 17773. doi: 10.1002/chem.v27.71
	(b) Zhu X.-J.; Wei J.; Hu C.-X.; Xiao Q.-T.; Cai L.-T.; Wang H.; Xie Y.-Y.; Sheng R. Eur. J. Org. Chem. 2022, e202200629.
	(c) Sheng H.-Y.; Su J.-K.; Li X.; Song Q.-L. CCS Chem. 2022, 4, 3820. doi: 10.31635/ccschem.022.202101576
[31]	Huang Y.-B.; Lin Z.-M.; Chen Y.; Fang S.-J.; Jiang H.-F.; Wu W.-Q. Org. Chem. Front. 2019, 6, 2462. doi: 10.1039/C9QO00506D
[32]	Kim Y.; Heo J.; Kim D.; Chang S.; Seo S. Nat. Commun. 2020, 11, 4761. doi: 10.1038/s41467-020-18557-8
[33]	Hayashi H.; Takano H.; Katsuyama H.; Harabuchi Y.; Maeda S.; Mita T. Chem. Eur. J. 2021, 27, 10040. doi: 10.1002/chem.v27.39
[34]	Zhu Z.; Krishnamurti V.; Ispizua-Rodriguez X.; Barrett C.; Prakash G. K. S. Org. Lett. 2021, 23, 6494. doi: 10.1021/acs.orglett.1c02305
[35]	Zhu Z.-Y.; Xu Y.-J.; Krishnamurti V.; Koch C. J.; Ispizua-Rodriguez X.; Barrett C.; Prakash G. K. S. J. Fluorine Chem. 2022, 261, 110023.
[36]	Song H.-H.; Li W.-H.; Wang X.-Y.; Wang K.-T.; Li J.-W.; Liu S.; Gao P.; Duan X.-H.; Hu J.-B.; Hu M.-Y. CCS Chem. 2023, DOI: 10.31635/ccschem.023.202302980.
[37]	(a) Levin V. V.; Zemtsov A. A.; Struchkova M. I.; Dilman A. D. Org. Lett. 2013, 15, 917. doi: 10.1021/ol400122k pmid: 26664635
	(b) Smirnov V. O.; Maslov A. S.; Levin V. V.; Struchkova M. I.; Dilman A. D. Russ. Chem. Bull. 2014, 63, 2564. doi: 10.1007/s11172-014-0778-1 pmid: 26664635
	(c) Zemtsov A. A.; Kondratyev N. S.; Levin V. V.; Struchkova M. I.; Dilman A. D. J. Org. Chem. 2014, 79, 818. doi: 10.1021/jo4024705 pmid: 26664635
	(d) Smirnov V. O.; Struchkova M. I.; Arkhipov D. E.; Korlyukov A. A.; Dilman A. D. J. Org. Chem. 2014, 79, 11819. doi: 10.1021/jo5023537 pmid: 26664635
	(e) Kondratyev N. S.; Levin V. V.; Zemtsov A. A.; Struchkova M. I.; Dilman A. D. J. Fluorine Chem. 2015, 176, 89. doi: 10.1016/j.jfluchem.2015.06.001 pmid: 26664635
	(f) Zemtsov A. A.; Volodin A. D.; Levin V. V.; Struchkova M. I.; Dilman A. D. Beilstein J. Org. Chem. 2015, 11, 2145. doi: 10.3762/bjoc.11.231 pmid: 26664635
	(g) Zemtsov A. A.; Kondratyev N. S.; Levin V. V.; Struchkova M. I.; Dilman A. D. Russ. Chem. Bull. 2016, 65, 2760. doi: 10.1007/s11172-016-1649-8 pmid: 26664635
	(h) Ashirbaev S. S.; Levin V. V.; Struchkova M. I.; Dilman A. D. J. Fluorine Chem. 2016, 191, 143. doi: 10.1016/j.jfluchem.2016.07.018 pmid: 26664635
[38]	(a) Wang J.-D.; Tokunaga E.; Shibata N. Chem. Commun. 2018, 54, 8881. doi: 10.1039/C8CC05135F
	(b) Wang Y.-K.; Wang S.-F.; Zhang C.-H.; Zhao T.; Hu Y.-Q.; Zhang M.-W.; Fu Y. Synlett 2021, 32, 1123. doi: 10.1055/a-1507-5878
	(c) Wang Y.-K.; Wang S.-F.; Qiu P.-Y.; Fang L.-Z.; Wang K.; Zhang Y.-W.; Zhao C.-H.; Zhao T. Org. Biomol. Chem. 2021, 19, 4788. doi: 10.1039/D1OB00511A
[39]	Xie Q.-Q.; Zhu Z.-Y.; Li L.-C.; Ni C.-F.; Hu J.-B. Angew. Chem., Int. Ed. 2019, 58, 6405. doi: 10.1002/anie.v58.19
[40]	(a) Hu M.-Y.; Ni C.-F.; Li L.-C.; Han Y.-X.; Hu J.-B. J. Am. Chem. Soc. 2015, 137, 14496. doi: 10.1021/jacs.5b09888
	(b) Zhang Z.-K.; Yu W.-Z.; Wu C.-G.; Wang C.-P.; Zhang Y.; Wang J.-B. Angew. Chem., Int. Ed. 2016, 55, 273. doi: 10.1002/anie.v55.1
[41]	(a) Fu X.-P.; Xue X.-S.; Zhang X.-Y.; Xiao Y.-L.; Zhang S.; Guo Y.-L.; Leng X.-B.; Houk K. N.; Zhang X.-G. Nat. Chem. 2019, 11, 948. doi: 10.1038/s41557-019-0331-9 pmid: 31548670
	(b) Zeng X.; Li Y.; Min Q.-Q.; Xue X.-S.; Zhang X.-G. Nat. Chem. 2023, 15, 1064. doi: 10.1038/s41557-023-01236-8 pmid: 31548670
[42]	Yang R.-Y.; Wang H.; Xu B. Chem. Commun. 2021, 57, 4831. doi: 10.1039/D1CC01132D
[43]	(a) Zhang R.; Zhang Z.-K.; Zhou Q.; Yu L.-F.; Wang J.-B. Angew. Chem., Int. Ed. 2019, 58, 5744. doi: 10.1002/anie.v58.17 pmid: 32633508
	(b) Zhang R.; Zhang Z.-K.; Wang K.; Wang J.-B. J. Org. Chem. 2020, 85, 9791. doi: 10.1021/acs.joc.0c01120 pmid: 32633508
[44]	Wang X.; Pan S.-T.; Luo Q.-Y.; Wang Q.; Ni C.-F.; Hu J.-B. J. Am. Chem. Soc. 2022, 144, 12202. doi: 10.1021/jacs.2c03104 pmid: 35786906
[45]	Supranovich V. I.; Levin V. V.; Struchkova M. I.; Korlyukov A. A.; Dilman A. D. Org. Lett. 2017, 19, 3215. doi: 10.1021/acs.orglett.7b01334 pmid: 28541046
[46]	Supranovich V. I.; Levin V. V.; Dilman A. D. Beilstein J. Org. Chem. 2020, 16, 1550. doi: 10.3762/bjoc.16.126 pmid: 32704320
[47]	(a) Liu L.; Aguilera M. C.; Lee W.; Youshaw C. R.; Neidig M. L.; Gutierrez O. Science 2021, 374, 432. doi: 10.1126/science.abj6005
	(b) Rentería-Gómez A.; Lee W.; Yin S.; Davis M.; Gogoi A. R.; Gutierrez O. ACS Catal. 2022, 12, 11547. doi: 10.1021/acscatal.2c03498
[48]	Ellefsen J. D.; Miller S. J. J. Org. Chem. 2022, 87, 10250. doi: 10.1021/acs.joc.2c01231
[49]	Choi K.; Mormino M. G.; Kalkman E. D.; Park J.; Hartwig J. F. Angew. Chem., Int. Ed. 2022, 61, e202208204.

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

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 43

References 49

Related Articles 12

Recommended Articles

Metrics

Comments

[1]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[2]	Jinxiao Zhao, Tonghui Wei, Sen Ke, Yi Li. Visible Light-Catalyzed Synthesis of Difluoroalkylated Polycyclic Indoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1102-1114.
[3]	Hua Huang, Xin Li, Jianke Su, Qiuling Song. Difluorocarbene-Enabled Synthesis of 3-Substituted-2-oxoindoles from o-Vinylanilines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1146-1156.
[4]	Xiang Chen, Wen-Tao Ouyang, Xiao Li, Wei-Min He. Visible-Light Induced Organophotocatalysis for the Synthesis of Difluoroethylated Benzoxazines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4213-4219.
[5]	Qi Sun, Zeying Sun, Ze Yu, Guangwei Wang. Nickel-Catalyzed Stereoselective Aryl-Difluoroalkylation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2515-2520.
[6]	Mengmeng Guo, Zilun Yu, Yulan Chen, Danhua Ge, Mengtao Ma, Zhiliang Shen, Xueqiang Chu. Difluorinated Silyl Enol Ethers as Fluorine-Containing Building Blocks for the Synthesis of Organofluorine Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3562-3587.
[7]	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.
[8]	Jun Pan, Jingjing Wu, Fanhong Wu. Progress in Fluoroalkylation of Multicomponent [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 983-1001.
[9]	Qin Wenbing, Chen Jiayi, Xiong Wei, Liu Guokai. Recent Advance in Development and Application of Electrophilic Difluoromethylating Reagents [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3177-3195.
[10]	Gao Xing, He Xu, Zhang Xingang. Nickel-Catalyzed Difluoromethylation of (Hetero)aryl Bromides with BrCF₂H [J]. Chin. J. Org. Chem., 2019, 39(1): 215-222.
[11]	Wang Weiqiang, Yu Qinwei, Zhang Qian, Li Jiangwei, Hui Feng, Yang Jianming, Lü Jian. Recent Progress on Difluoromethylation Methods [J]. Chin. J. Org. Chem., 2018, 38(7): 1569-1585.
[12]	Zhang Ji, Jin Chuanfei, Zhang Yingjun. Recent Advances in Research and Development of Fluorinated Drugs and New Methods for Fluorination, Mono-, Di-and Tri-fluoromethylation [J]. Chin. J. Org. Chem., 2014, 34(4): 662-680.