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三溴化硼催化的反应类型及其机理的研究进展
Research Progress on Boron Tribromide-Catalyzed Reaction Types and Mechanisms

DOI: 10.12677/jocr.2026.141001, PP. 1-14

Keywords: 三溴化硼,裂解,硼氢化,溴代,环化
Boron Tribromide
, Cracking, Brown Hydroboration, Bromination, Cyclization

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Abstract:

三溴化硼是一种常用的无机化合物,作为催化剂被应用于聚合物化学,天然产物合成和药物化学等领域,涉及到了多样的有机化学反应类型,本文主要综述了三溴化硼催化的C-H硼氢化反应、醚和胺及硫醇的裂解、溴代和环化等方面,并对其中相关的催化反应机理简单论述。
Boron tribromide is a commonly used inorganic compound. It is applied as a catalyst in different fields involving various types of organic chemical reactions, such as polymer chemistry, natural product synthesis, and medicinal chemistry. This article mainly reviews the C-H borohydride reaction, cracking of ether, amine and thiol, bromination, and cyclization catalyzed by boron tribromide, and briefly discusses the related catalytic reaction mechanisms.

References

[1]  Iqbal, S.A., Millet, C.R.P., Pahl, J., Yuan, K. and Ingleson, M.J. (2022) Two Directing Groups Used for Metal Catalysed Meta‐C-H Functionalisation Only Effect ortho Electrophilic C-H Borylation. European Journal of Organic Chemistry, 2022, e202200901.
https://doi.org/10.1002/ejoc.202200901
[2]  Wakamiya, A., Taniguchi, T. and Yamaguchi, S. (2006) Intramolecular B-N Coordination as a Scaffold for Electron‐transporting Materials: Synthesis and Properties of Boryl‐Substituted Thienylthiazoles. Angewandte Chemie, 118, 3242-3245.
https://doi.org/10.1002/ange.200504391
[3]  Ishida, N., Moriya, T., Goya, T. and Murakami, M. (2010) Synthesis of Pyridine-Borane Complexes via Electrophilic Aromatic Borylation. The Journal of Organic Chemistry, 75, 8709-8712.
https://doi.org/10.1021/jo101920p
[4]  Lv, J., Zhao, B., Yuan, Y., Han, Y. and Shi, Z. (2020) Boron-Mediated Directed Aromatic C-H Hydroxylation. Nature Communications, 11, Article No. 1316.
https://doi.org/10.1038/s41467-020-15207-x
[5]  Lv, J., Chen, X., Xue, X., Zhao, B., Liang, Y., Wang, M., et al. (2019) Metal-Free Directed sp2-C-H Borylation. Nature, 575, 336-340.
https://doi.org/10.1038/s41586-019-1640-2
[6]  Wu, G., Fu, X., Wang, Y., Deng, K., Zhang, L., Ma, T., et al. (2020) C-H Borylation of Diphenylamines through Adamantane-1-Carbonyl Auxiliary by BBr3. Organic Letters, 22, 7003-7007.
https://doi.org/10.1021/acs.orglett.0c02552
[7]  Lv, J., Liang, Y., Ouyang, Y. and Zhang, H. (2024) Metal-Free ortho C-H Borylation of Thiobenzamides. Organic Letters, 26, 3709-3714.
https://doi.org/10.1021/acs.orglett.4c00691
[8]  Guo, Y., Wang, M. and Liu, G. (2024) Recent Advances on Regioselective C-H Borylation of Indoles. Asian Journal of Organic Chemistry, 13, e202400464.
https://doi.org/10.1002/ajoc.202400464
[9]  Hata, H., Yamaguchi, S., Mori, G., Nakazono, S., Katoh, T., Takatsu, K., et al. (2007) Regioselective Borylation of Porphyrins by C-H Bond Activation under Iridium Catalysis to Afford Useful Building Blocks for Porphyrin Assemblies. Chemistry—An Asian Journal, 2, 849-859.
https://doi.org/10.1002/asia.200700086
[10]  Kosak, T.M., Conrad, H.A., Korich, A.L. and Lord, R.L. (2015) Ether Cleavage Re‐Investigated: Elucidating the Mechanism of BBr3‐Facilitated Demethylation of Aryl Methyl Ethers. European Journal of Organic Chemistry, 2015, 7460-7467.
https://doi.org/10.1002/ejoc.201501042
[11]  Gan, B., Jiang, X., Mi, Z., Zhang, C., Bai, R., Shuai, Q., et al. (2019) Straightforward Synthesis of Amino-3-Hydroxypyridin-4-One Iron Chelators via BBr3-Mediated Tandem Reduction of Azides and Deprotection of Methyl Ether. Synthetic Communications, 49, 73-79.
https://doi.org/10.1080/00397911.2018.1542002
[12]  Vo, D.D. and Elofsson, M. (2016) Total Synthesis of Viniferifuran, Resveratrol‐Piceatannol Hybrid, Anigopreissin A and Analogues—Investigation of Demethylation Strategies. Advanced Synthesis & Catalysis, 358, 4085-4092.
https://doi.org/10.1002/adsc.201601089
[13]  Krohn, K., Aslan, A., Ahmed, I., Pescitelli, G. and Funaioli, T. (2009) Novel 1,4,5,8‐Phenanthrenediquinones and Unusual Deoxygenation with Trimethylsilyl Iodide. European Journal of Organic Chemistry, 2009, 5452-5457.
https://doi.org/10.1002/ejoc.200900666
[14]  Bellur, E. and Langer, P. (2005) Convenient Synthesis of ε-Halo-β-Ketoesters and γ,γ‘-Dibromoalkanones by Regio-And Chemoselective Reaction of 2-Alkylidenetetrahydrofurans with Boron Trihalides: A “Ring-Closure/Ring-Cleavage” Strategy. The Journal of Organic Chemistry, 70, 3819-3825.
https://doi.org/10.1021/jo047824+
[15]  Sotelo, E., Coelho, A. and Raviña, E. (2001) Pyridazines. Part 25: Efficient and Selective Deprotection of Pharmacologically Useful 2-Mom-Pyridazinones Using Lewis Acids. Tetrahedron Letters, 42, 8633-8636.
https://doi.org/10.1016/s0040-4039(01)01898-6
[16]  Paliakov, E. and Strekowski, L. (2004) Boron Tribromide Mediated Debenzylation of Benzylamino and Benzyloxy Groups. Tetrahedron Letters, 45, 4093-4095.
https://doi.org/10.1016/j.tetlet.2004.03.139
[17]  Stuhr-Hansen, N. (2003) The Tert-Butyl Moiety—A Base Resistent Thiol Protecting Group Smoothly Replaced by the Labile Acetyl Moiety. Synthetic Communications, 33, 641-646.
https://doi.org/10.1081/scc-120015820
[18]  Yamato, T., Fujimoto, M., Miyazawa, A. and Matsuo, K. (1997) Selective Preparation of Polycyclic Aromatic Hydrocarbons. Part 5.1 Bromination of 2,7-Di-Tert-Butylpyrene and Conversion into Pyrenoquinones and Their Pyrenoquinhydrones. Journal of the Chemical Society, Perkin Transactions 1, No. 8, 1201-1208.
https://doi.org/10.1039/a606200h
[19]  Waldman, S.R., Monte, A.P., Bracey, A. and Nichols, D.E. (1996) One-Pot Claisen Rearrangement/O-Methylation/Alkene Isomerization in the Synthesis of Ortho-Methoxylated Phenylisopropylamines. Tetrahedron Letters, 37, 7889-7892.
https://doi.org/10.1016/0040-4039(96)01807-2
[20]  Hara, S. and Suzuki, A. (1991) The Organic Synthesis Using Haloboration Reaction 20. a Simple Synthesis of (2-Bromoallyl)Diphenoxyborane by the Bromoboration of Allene and Its Reaction with Carbonyl Compounds. Tetrahedron Letters, 32, 6749-6752.
https://doi.org/10.1016/s0040-4039(00)93593-7
[21]  Polášek, J., Paciorek, J., Stošek, J., Semrád, H., Munzarová, M. and Mazal, C. (2020) Stereoselective Bromoboration of Acetylene with Boron Tribromide: Preparation and Cross-Coupling Reactions of (Z)-Bromovinylboronates. The Journal of Organic Chemistry, 85, 6992-7000.
https://doi.org/10.1021/acs.joc.0c00341
[22]  Kabalka, G.W., Wu, Z. and Ju, Y. (2002) A New Reaction of Aryl Aldehydes with Aryl Acetylenes in the Presence of Boron Trihalides. Organic Letters, 4, 1491-1493.
https://doi.org/10.1021/ol025696a
[23]  Gieuw, M.H., Chen, S., Ke, Z., Houk, K.N. and Yeung, Y. (2020) Boron Tribromide as a Reagent for Anti-Markovnikov Addition of HBr to Cyclopropanes. Chemical Science, 11, 9426-9433.
https://doi.org/10.1039/d0sc02567d
[24]  Qin, Y., Qi, L., Zhen, X., Wang, X., Chai, H., Ma, X., et al. (2023) Different Performances of BF3, BCl3, and BBr3 in Hypervalent Iodine-Catalyzed Halogenations. The Journal of Organic Chemistry, 88, 4359-4371.
https://doi.org/10.1021/acs.joc.2c02967
[25]  Otsuka, H., Araki, K. and Shinkai, S. (1995) Syntheses of All Poasible Calix[6]arene Derivatives with Meo-and ROCOCH2O-Substituents and Their Metal Binding Properties. Tetrahedron, 51, 8757-8770.
https://doi.org/10.1016/0040-4020(95)00466-l
[26]  Mataka, S., Liu, G., Sawada, T., Kurisu, M. and Tashiro, M. (1994) Photothermal Side-Chain Bromination of Methyl-, Dimethyl-, and Trimethylbenzenes with N-Bromosuccinimide. Bulletin of the Chemical Society of Japan, 67, 1113-1119.
https://doi.org/10.1246/bcsj.67.1113
[27]  Chen, H., Yin, J. and Lin, Y. (2009) Mild and Efficient Conversion of Trifluoromethylarenes into Tribromomethylarenes Using Boron Tribromide. Chemical Papers, 63, 92-96.
https://doi.org/10.2478/s11696-008-0082-3
[28]  申理滔, 陈红飙, 林原斌. 甲基芳烃的侧链溴化新方法研究[J]. 有机化学, 2010, 30(2): 272-275.
[29]  Chen, H., Shen, L. and Lin, Y. (2010) Benzylic Bromination of Toluene Derivatives with Boron Tribromide. Synthetic Communications, 40, 998-1003.
https://doi.org/10.1080/00397910903029917
[30]  Pelletier, J.D. and Poirier, D. (1994) Bromination of Alcohols by Boron Tribromide. Tetrahedron Letters, 35, 1051-1054.
https://doi.org/10.1016/s0040-4039(00)79963-1
[31]  Sprott, K.T. and Corey, E.J. (2003) A New Cationic, Chiral Catalyst for Highly Enantioselective Diels-Alder Reactions. Organic Letters, 5, 2465-2467.
https://doi.org/10.1021/ol034706k
[32]  Wang, J., Wu, X., Wang, B., Yuan, X., Yang, S. and Hu, H. (2024) The Catalytic Synthesis of α‐Bromo Aryl Acetic Acids by Late‐Stage Bromination. European Journal of Organic Chemistry, 27, e202400962.
https://doi.org/10.1002/ejoc.202400962
[33]  Shen, L., Chen, H. and Lin, Y. (2010) A New Method for α-Bromination of Methylarene. Chinese Journal of Organic Chemistry, 30, 272-275.
[34]  Huang, K., Cai, J., Wang, R., Zhang, Y., Wang, B., Xia, Y., et al. (2024) Electrochemical C(sp2)—H Bromination of Glycine Derivatives Enabled by Boron. Chinese Journal of Organic Chemistry, 44, 989-996.
https://doi.org/10.6023/cjoc202308018
[35]  Jourdan, J., Rochais, C., Legay, R., Sopkova de Oliveira Santos, J. and Dallemagne, P. (2013) An Unusual Boron Tribromide-Mediated, One-Pot Bromination/Cyclization Reaction. Application to the Synthesis of a Highly Strained Cyclopenta[1,3]Cyclopropa[1,2-B]Pyrrolizin-8-One. Tetrahedron Letters, 54, 1133-1136.
https://doi.org/10.1016/j.tetlet.2012.12.056
[36]  Bellur, E. and Langer, P. (2005) Synthesis of Benzofurans with Remote Bromide Functionality by Domino “Ring-Cleavage-Deprotection-Cyclization” Reactions of 2-Alkylidenetetrahydrofurans with Boron Tribromide. The Journal of Organic Chemistry, 70, 7686-7693.
https://doi.org/10.1021/jo051079z
[37]  Kamlar, M., Henriksson, E., Císařová, I., Malo, M. and Sundén, H. (2021) Synthesis of Cis-Oriented Vicinal Diphenylethylenes through a Lewis Acid-Promoted Annulation of Oxotriphenylhexanoates. The Journal of Organic Chemistry, 86, 8660-8671.
https://doi.org/10.1021/acs.joc.1c00445
[38]  Yao, C., Zhang, J., Zhang, J., Kang, Y. and Shi, J. (2016) A Facile and Practical Total Synthetic Route for Ampelopsin F and Permethylated Ε-viniferin. Synlett, 27, 1587-1591.
https://doi.org/10.1055/s-0035-1561419

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