环硼氮烷及其衍生物的合成与官能团化研究进展

doi:10.6023/cjoc202605024

摘要/Abstract

环硼氮烷是一种具有独特结构和性质的无机化合物,又被称为“无机苯”。具有独特的B-N等电子结构、高热稳定性、丰富的位点可修饰特性以及可调的电子性质。本文综述了环硼氮烷及其衍生物的合成方法及官能团化反应,讨论了通过简单前体直接合成官能化环硼氮烷衍生物的策略,重点介绍了其烃基化（烷基化、烯基化、炔基化、芳基化）、烃氧基化、氯化、溴化、胺化及与硅氮烷的反应等。论文还分析了当前研究中面临的挑战,提出了未来的研究方向,为环硼氮烷衍生物在多领域的发展提供理论参考与研发思路。

关键词: 环硼氮烷, 环硼氮烷合成, 官能化环硼氮烷衍生物, 有机反应

Borazine are inorganic compounds with unique structures and properties, also known as “inorganic benzene”. It possesses a unique B-N electronic structure, high thermal stability, a wide range of modifiable sites, and tunable electronic properties. This paper reviews the synthetic methods and functionalization reactions of borazines and their derivatives, focusing on strategies for the direct synthesis of functionalized borazine derivatives from simple precursors. It highlights their alkylation, alkenylation, alkynylation, arylation, alkoxylation, chlorination, bromination, amination, and reactions with silazanes. This paper also analyzes the challenges in current research and proposes the future research directions, providing theoretical basis and R & D idea of the molecular design of borazine derivatives.

Key words: borazine, synthesis of borazine, functionalized borazine derivatives, organic reactions

引用此文

冯嘉婷, 王梓宇, 付雪薇, 王柏文, 江焕峰. 环硼氮烷及其衍生物的合成与官能团化研究进展[J]. 有机化学, doi: 10.6023/cjoc202605024.

Feng Jiating, Wang Ziyu, Fu Xuewei, Wang Bowen, Jiang Huanfeng. Recent Advances in the Synthesis and Functionalization of Borazine and Its Derivatives[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202605024.

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参考文献

[1] Stock A.; Pohland, E. Ber. Dtsch. Chem. Ges. (A and B Series).1926, 59, 2215.
[2] Harshbarger W.; Lee G.; Porter R. F.; Bauer, S. H. Inorg. Chem.1969, 8, 1683.
[3] Shen S.; Lu Z. X.; Duan, Y. T. Liaoning Chem. Ind.2023, 52, 1633 (in Chinese).
(沈绥, 卢振西, 段玉婷, 辽宁化工, 2023, 52, 1633.)
[4] Wiberg E.; Bolz, A. Ber. Dtsch. Chem. Ges. A/B1940, 73, 209.
[5] (a) Báez-Grez R.; Pino-Rios R. RSC Adv.2022, 12, 7906.
(b) Ota K.; Kinjo, R. Chem. Asian J.2020, 15, 2558.
[6] Kiran B.; Phukan A. K.; Jemmis, E. D. Inorg. Chem.2001, 40, 3615.
[7] Islas R.; Chamorro E.; Robles J.; Heine T.; Santos J. C.; Merino G. Struct. Chem.2007, 18, 833.
[8] Schleyer P. V. R.; Jiao H.; Hommes N. J. R. V.; Malkin V. G.; Malkina, O. L. J. Am. Chem. Soc.1997, 119, 12669.
[9] Tossel J. A.; Moore J. H.; McMillan K.; Subramaniam C. K.; Coplan, M. A. J. Am. Chem. Soc.1992, 114, 1114.
[10] Wiberg E.; Bolz, A. Ber. Dtsch. Chem. Ges. (A and B Series)1940, 73, 209.
[11] McConnell C. R.; Liu S. Y.; Chem. Soc. Rev.2019, 48, 3436.
[12] Marchionni D.; Basak S.; Khodadadi A. N.; Marrocchi A.; Vaccaro, L. Adv. Funct. Mater.2023, 33, 2303635.
[13] Campbell P. G.; Marwitz A. J. V.; Liu, S. Y. Angew. Chem., Int. Ed.2012, 51, 6074.
[14] Neogi I.; Szpilman A. M.Synthesis (Stuttg) 2022, 54, 1877.
[15] Yang S.; Lian K.; Tian P.; Lu D.; Zhang J.Colloids Surf. A: Physicochemical Engineering Aspects 2024, 702, 135103.
[16] Kubota Y.; Watanabe K.; Tsuda O.; Taniguchi T. Science2007, 317, 932.
[17] Weng Q.; Wang X.; Wang X.; Bando Y.; Golberg D.Chem. Soc. Rev. 2016, 45, 3989.
[18] (a) Kaldor, A. J. Chem. Phys.1971, 55, 4641.
(b) Frost D. C.; Herring F. G.; McDowell C. A.; Stenhouse, I. A. Chem. Phys. Lett.1970, 5, 291.
(c) Al-Joboury, M. I.; Turner, D. W.J. Chem. Soc. 1964, 4434.
[19] Soares G. P.; Guerini, S. J. Modern Phys.2011, 2, 857.
[20] Watanabe K.; Taniguchi T.; Niiyama T.; Miya K.; Taniguchi M. Nat. Photonics2009, 3, 591.
[21] Li J.; Lin J.; Xu X.; Zhang X.; Xue Y.; Mi J.; Mo Z.; Fan Y.; Hu L.; Yang X.; Zhang J.; Meng F.; Yuan S.; Tang C. Nanotechnology,2013, 24, 155603.
[22] Lorenzo-García M. M.; Bonifazi D. Chimia (Aarau)2017, 71, 550.
[23] Bonifazi D.; Fasano F.; Lorenzo-Garcia M. M.; Marinelli D.; Oubaha H.; Tasseroul J. Chem. Commun.2015, 51, 15222.
[24] Kho J.; Moon K.; Kim J.; Kim D.J. Am. Ceram. Soc. 2000, 83, 2681.
[25] Song L.; Ci L.; Lu H.; Sorokin P. B.; Jin C.; Ni J.; Kvashnin A. G.; Kvashnin D. G.; Lou J.; Yakobson B. I.; Ajayan, P. M. Nano Lett.2010, 10, 3209.
[26] Jhi S.; Kwon, Y. Phys. Rev. B: Condens. Matter Mater. Phys.2004, 69, 245407.
[27] Lei W.; Portehault D.; Liu D.; Qin S.; Chen Y. Nat. Commun.2013, 4, 1777.
[28] Sun Q.; Li Z.; Searles D. J.; Chen Y.; Lu G. M.; Du, A. J. Am. Chem. Soc.2013, 135, 8246.
[29] (a) Brown, C. A.; Laubengayer, A. W. J. Am. Chem. Soc. 1955, 77, 3699.
(b) Rothgery E. F.; Hohnstedt, L. F. Inorg. Chem.1967, 6, 1065.
(c) Hohnstedt L. F.; Haworth, D. T. J. Am. Chem. Soc.1960, 82, 89.
(d) Zhakharkin L. I.; Ol'shevskaya, V. A. Synth. React. Inorg. Met.-Org. Chem.1996, 26, 921.
(e) Schaeffer R.; Steindler M.; Hohnstedt L.; Smith, H. S. Jr.; Eddy L. B.; Schlesinger, H. I. J. Am. Chem. Soc.1954, 76, 3303.
[30] Hough, William V.US 4150097, 1979.
[31] Wideman T.; Sneddon, L. G. Inorg. Chem.1995, 34, 1002.
[32] Jacka C. A.; Temple K. T.; Lough A. J.; Manners I. Chem.Commun.2001, 11, 962.
[33] Lu Z.; Schweighauser L.; Hausmann H.; Wegner, H. A. Angew. Chem. Int. Ed.2015, 54, 15556.
[34] Schlesinger H. I.; Horvitz L.; Burg, A. B. J. Am. Chem. Soc.1936, 58, 409.
[35] Aubrey D. W.; Lappert M. F.J. Chem. Soc. 1959, 2927.
[36] Cornu D.; Bernard S.; Duperrier S.; Toury B.; Miele, P. J. Eur. Ceram. Soc.2005, 25, 111.
[37] Narula C. K.; Schaeffer R.; Datye A. K.; Borek T. T.; Rapko B. M.; Paine, R. T. Chem. Mater.1990, 2, 384.
[38] Emeléus H. J.; Wade K.J. Chem. Soc. 1960, 2614.
[39] Hawthorne M F. J. Am. Chem. Soc.1961, 83, 833.
[40] Fritz P.; Niedenzu K.; Dawson, J. W. Inorg. Chem.1964, 3, 626.
[41] Brown M. P.; Heseltine R. W.; Sutcliffe L. H.J. Chem. Soc. A 1968, 612.
[42] Framery E.; Vaultier M.Heteroatom Chem. 2000, 11, 218.
[43] Yamamoto Y.; Miyamoto K.; Umeda J.; Nakatani Y.; Yamamoto T.; Miyaura, N. J. Organomet. Chem.2006, 691, 4909.
[44] Stpanenko V.; Ortiz-Marciales M.; Barnes C. E.; Garcia C. Tetrahedron Lett.2006, 47, 7603.
[45] Köster R.; Hattori S.; Morita, Y. Angew. Chem. Int. Ed. Engl.1965, 4, 695.
[46] Köster R.; Bellut H.; Hattori, S. Justus L. A. Chem.1968, 720, 1.
[47] Biswas S.; Müller M.; Tönshoff C.; Eichele K.; Maichle-Mössmer C.; Ruff A.; Speiser B.; Bettinger, H. F. Eur. J. Org. Chem.2012, 24, 4634.
[48] Krieg M.; Reichter F.; Haiss P.; Ströbele M.; Eichele K.; Treanor M.-J.; Schaub R.; Bettinger, H. F. Angew. Chem. Int. Ed.2015, 54, 8284.
[49] Müllen K.; Rabe, J. P. Acc. Chem. Res.2008, 41, 511.
[50] Müller M.;Maichle-Mössmer, C.; Sirsch, P.; Bettinger, H. F. ChemPlusChem 2013, 78, 988.
[51] Bartlett R. K.; Turner H. S.; Warne R. J.; Young M. A.; Lawrenson I. J.[J].Chem. Soc. A 1966, 479.
[52] Sánchez-Sánchez C.; Brüller S.; Sachdev H.; Müllen K.; Krieg M.; Bettinger H. F.; Nicolai A.; Meunier V.; Talirz L.; Fasel R.; Ruffieux P. ACS Nano2015, 9, 9228.
[53] Culling G. C.; Dewar M. J.S.; Marr, P. A. J. Am. Chem. Soc. 1964, 86, 1125.
[54] Luo W.; Zakharov L. N.; Liu S.Y.J. Am. Chem. Soc. 2011, 133, 13006.
[55] Luo W.; Neiner D.; Karkamkar A.; Parab K.; Garner, E. B., III; Dixon, D. A.; Matson D.; Autrey T.; Liu S.Y. Dalton Trans.2013, 42, 611.
[56] Blanchard US 5316986, 1993.
[57] Haberecht J.; Krummland A.; Breher F.; Gebhardt B.; Rüegger H.; Nesper R.; Grützmacher H.Dalton Trans. 2003, 11, 2126.
[58] (a) Blanchard C.; Framery E.; Vaultier M. Synthesis1996, 1, 45.
(b) Blanchard, C.; Vaultier, M.; Mortier, [J].Tetrahedron Lett. 1997, 38, 8863.
[59] Guo K.; Qi H.; Wang F.; Zhu, Y. Mater. Sci. Eng. B2014, 186, 7.
[60] Grenda S.; Claiser N.; Barbon A.; Guégan F.; Toury B.; Luneau, D. J. Am. Chem. Soc.2024, 146, 32906.
[61] (a) Buchmeiser, M. R. Chem. Rev. 2000, 100, 1565.
(b) Luh T.-Y.; Leung M.-K.; Wong K.-T. Chem. Rev.2000, 100, 3187.
[62] Jaska C. A.; Temple K.; Lough A. J.; Manners I.Chem. Commun. 2001, 11, 962.
[63] Dorn H.; Singh R. A.; Massey J. A.; Lough A. J.; Manners, I. Angew. Chem. Int. Ed.1999, 38, 3321.
[64] Jaska C. A.; Temple K.; Lough A. J.; Manners, I. J. Am. Chem. Soc.2003, 125, 9424.
[65] Sloan M. E.; Clark T. J.; Manners I. Inorg. Chem.2009, 48, 2429.
[66] Kawano Y.; Uruichi M.; Shimoi M.; Taki S.; Kawaguchi T.; Kakizawa T.; Ogino, H. J. Am. Chem. Soc.2009, 131, 14946.
[67] Burg A. B.; Randolph, C. L. J. Am. Chem. Soc.1949, 71, 3451.
[68] Sloan M. E.; Staubitz A.; Clark T. J.; Russell C. A.; Lloyd-Jones G. C.; Manners, I. J. Am. Chem. Soc.2010, 132, 3831.
[69] Vance J. R.; Robertson A. P.M.; Lee, K.; Manners, I.Chem. Eur. J. 2011, 17, 4099.
[70] Hurt P.; Gamboa-Carballo J. J.; Schweinzer C.; Himmelbauer D.; Thöny D.; Gianetti T. L.; Trincado M.; Grützmacher H. Dalton Trans.2024, 53, 14212.
[71] Smalley J. H.; Stafiej, S. F. J. Am. Chem. Soc.1959, 81, 582.
[72] Fazen P. J.; Sneddon L. G. Organometallics.1994, 13, 2867.
[73] Fazen P. J. Chem. Mater. 1995, 7, 1942.
[74] Lynch A. T.; Sneddon, L. G. J. Am. Chem. Soc.1987, 109, 5867.
[75] Lynch A. T.; Sneddon, L. G. J. Am. Chem. Soc.1989, 111, 6201.
[76] Jackson L. A.; Allen C. W.J. Chem. Soc., Perkin Trans. 1. 1990, 2423.
[77] Peng X.; Wang K. Q.; Guo K. K.; Zhu Y. P.; Wang F.; Sun Y. L.; Lei K.; Qi, H. M. Chin. J. Inorg. Chem.2023, 39, 381 (in Chinese).
(彭翔, 王凯奇, 郭康康, 朱亚平, 王帆, 孙云龙, 雷昆, 齐会民, 无机化学学报, 2023, 39, 381.)
[78] Yamamoto, Y. JP2010-280637A, 2010 [Chem. Abstr. 2010, 154, 123456].
[79] Haworth D. T.; Hohnstedt, L. F. J. Am. Chem. Soc.1959, 81, 842.
[80] Ding, L. Z. Sci. Technol. Chem. Ind.2002, 10, 54 (in Chinese).
(丁亮中, 化工科技, 2002, 10, 54.)
[81] Riley R. F.; Schack, C. J. Inorg. Chem.1964, 3, 1651.
[82] Kreutzberger A.; Ferris, F. C. J. Org. Chem.1965, 30, 360.
[83] Wideman T.; Sneddon, L. G. Chem. Mater.1996, 8, 3.
[84] Sneddon, L. G; Remsen, E. E.; Zank, G. A. Chem. Mater.1993, 5, 547.
[85] Wideman T.; Su K.; Remsen, E. E. Chem. Mater.1995, 7, 2203.