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. 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, 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, 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. The synthetic methods and functionalization reactions of borazines and their derivatives are reviewed, focusing on direct synthetic strategies for functionalized borazines from simple precursors. It highlights their alkylation, alkenylation, alkynylation, arylation, alkoxylation, chlorination, bromination, amination, and reactions with silazanes. This review also analyzes the challenges in current‑day research and proposes future research directions, providing a theoretical basis and research‑and‑development ideas for the molecular design of borazine derivatives.

Key words: borazine, synthesis, 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, 2026, 46(9): 3372-3389.

Jiating Feng, Ziyu Wang, Xuewei Fu, Bowen Wang, Huanfeng Jiang. Recent Advances in the Synthesis and Functionalization of Borazine and Its Derivatives[J]. Chinese Journal of Organic Chemistry, 2026, 46(9): 3372-3389.

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图/表 45

图1. 环硼氮烷与苯的结构

Figure 1. Structures of borazine and benzene

图式1. Stock的环硼氮烷合成路线

Scheme 1. Stockʼs synthetic route to borazine

图式2. B,B',B"-三氯环硼氮烷还原成环硼氮烷的路线

Scheme 2. Route for the reduction of B,B',B"-trichloroborazine to borazine

图式3. 氨硼烷热解形成环硼氮烷

Scheme 3. Formation of borazine from pyrolysis of ammonia borane

图式4. (NH4)2SO4和NaBH4反应合成环硼氮烷

Scheme 4. Synthesis of borazine from the reaction of (NH4)2- SO4 and NaBH4

图式5. 氨硼烷热分解合成环硼氮烷

Scheme 5. Synthesis of borazine via thermal decomposition of ammonia borane

图式6. 化合物6在化合物11催化下脱氢制备环硼氮烷

Scheme 6. Dehydrogenative synthesis of borazine from 6 catalyzed by 11

图式7. 甲基乙硼烷与氨一步反应形成取代环硼氮烷衍生物

Scheme 7. One-step reaction of methyldiborane with ammonia to form substituted borazine derivatives

图式8. B(NHCH3)3热解脱MeNH2形成聚合物

Scheme 8. Thermal elimination of MeNH2 from B(NHCH3)3 to form a polymer

图式9. 19的合成及聚合

Scheme 9. Synthesis and polymerization of 19

图式10. 烷基腈与乙硼烷热解合成N,N',N"-三烷基取代环硼氮烷

Scheme 10. Synthesis of N,N',N"‑trialkyl‑substituted borazine by pyrolysis of alkyl nitrile and diborane

图式11. 热解三甲胺基硼烷合成B,B',B"-三烷基环硼氮烷

Scheme 11. Synthesis of B,B',B"‑trialkylborazine by pyrolysis of trimethylamine borane

图式12. 乙烯基二溴硼烷与仲胺加合物加热氨解制备B,B',B"-三乙烯基环硼氮烷

Scheme 12. Preparation of B,B',B"‑trivinylborazine by heating ammonolysis of the adduct of vinyldibromoborane and secondary amine

图式13. 伯胺与硼烷二甲基硫化物合成N,N',N"-三取代环硼氮烷

Scheme 13. Synthesis of N,N',N"‑trisubstituted borazine from primary amine and borane-dimethyl sulfide

图式14. 加热氨解双(二异丙胺)硼烷合成B,B',B"-三取代环硼氮烷

Scheme 14. Synthesis of B,B',B"‑trisubstituted borazine by heating ammonolysis of bis(diisopropylamine)borane

图式15. NaBH4、MeNH2和BF3•OEt2制备40

Scheme 15. Preparation of 40 from NaBH4, MeNH2, and BF3•OEt2

图式16. (a)由取代氨基醇和BH3•DMS加合物合成手性环硼氮烷; (b)由2-氨基苯酚和BH3•DMS合成非手性环硼氮烷

Scheme 16. (a) Synthesis of chiral borazine from substituted amino alcohol and BH3•DMS adduct; (b) Synthesis of achiral borazine from 2‑aminophenol and BH3•DMS

图式17. 有机伯胺与三乙胺硼烷加合物加热脱氢偶联制备取代环硼氮烷: (a) 2-氨基联苯; (b)苯胺; (c) α-萘胺

Scheme 17. Preparation of substituted borazines by thermal dehydrogenative coupling of organic primary amines with triethylamine borane adduct: (a) 2‑aminobiphenyl; (b) aniline; (c) α‑naphthylamine

图2. 9,10-菲炔和9,10-氮硼菲的结构

Figure 2. Structures of 9,10-phenanthryne and 9,10-azabora- phenanthrene

图式18. Bettinger通过脱氢卤化法合成三联苯基环硼氮烷

Scheme 18. Synthesis of terphenylborazine by Bettinger via de- hydrohalogenation

图式19. 59的合成

Scheme 19. Synthesis of 59

图式20. 三联苯基环硼氮烷溴化反应

Scheme 20. Bromination of terphenylborazine

图式21. BCl3与胺的反应过程

Scheme 21. Reaction process of BCl3 with amines

图式22. (a) 4-溴苯胺与BBr3制备70; (b) 70在Ag(111)表面芳基偶联形成2D网络

Scheme 22. (a) Preparation of 70 from 4‑bromoaniline and BBr3; (b) Aryl coupling of 70 on Ag(111) surface to form a 2D network

图式23. (a) 71热解合成72; (b) 73热解或通过催化剂辅助热解合成74

Scheme 23. (a) Synthesis of 72 by pyrolysis of 71; (b) Synthesis of 74 by pyrolysis or catalyst-assisted pyrolysis of 73

图式24. 二异丙胺、BCl3、乙炔和正丁基锂合成B,B',B"-三乙炔基环硼氮烷

Scheme 24. Synthesis of B,B',B"‑triethynylborazine from diisopropylamine, BCl3, acetylene, and n‑butyllithium

图式25. 格氏试剂取代B,B',B"-三氯环硼氮烷构建环硼氮烷衍生物

Scheme 25. Synthesis of borazine derivatives via substitution of B,B',B"‑trichloroborazine with Grignard reagents

图式26. 87的合成路线

Scheme 26. Synthetic route of 87

图式27. [Rh(1,5-cod)(µ-Cl)]2催化伯胺硼烷加合物脱氢偶联形成N,N',N"-三取代环硼氮烷: (a)烷基化; (b)芳基化

Scheme 27. Dehydrogenative coupling of primary amine borane adducts catalyzed by [Rh(1,5‑cod)(μ‑Cl)]2 to form N,N',N"‑trisub- stituted borazine: (a) Alkylation; (b) Arylation

图式28. 过渡金属催化伯胺硼烷加合物合成N,N',N"-三取代环硼氮烷: (a)使用M(CO)6催化的光化学环化反应; (b)使用[{CpFe(CO)2}2]催化的光化学环化反应

Scheme 28. Transition metal‑catalyzed synthesis of N,N',N"‑ trisubstituted borazine from primary amine borane adducts: (a) Photochemical cyclization catalyzed by M(CO)6; (b) Photochemical cyclization catalyzed by [{CpFe(CO)2}2]

图式29. (a)氨硼烷与铑-烯烃配合物(P=PPh2)的脱氢反应; (b)铑-烯烃配合物催化的N-炔丙胺硼烷转化合成97

Scheme 28. (a) Dehydrogenation of ammonia borane with rhodium olefin complexes (P=PPh2); (b) Rhodium-olefin complex- catalyzed synthesis of 97 from N-propargylamine-borane conversion

图式30. B-烷基化的N,N',N"-三取代环硼氮烷合成路线

Scheme 30. Synthesis route of B-alkylated N,N',N"-trisubsti- tuted borazine

图式31. (a) B-取代的单烷基、二烷基和三烷基环硼氮烷合成路线; (b)环硼氮烷与1-丁烯、顺式-2-丁烯和反式-2-丁烯反应

Scheme 31. (a) Synthesis route of B-substituted monoalkyl, dialkyl, and trialkyl borazine; (b) Reaction of borazine with 1-butene, cis-2-butene, and trans-2-butene

图式32. RhH(CO)(PPh3)3催化的环硼氮烷与乙烯基芳烃的反应路线

Scheme 32. RhH(CO)(PPh3)3-catalyzed reaction of borazine with vinyl aromatics

图式33. (a) RhH(CO)(PPh3)3催化的环硼氮烷与炔烃的反应路线; (b) PdBr2催化环硼氮烷及N,N',N"-三甲基环硼氮烷与烯烃的反应路线

Scheme 33. (a) RhH(CO)(PPh3)3-catalyzed reaction of borazine with alkynes; (b) PdBr2 catalyzed reaction of borazine and N,N',N"- trimethyl borazine with alkenes

图式34. 不对称B-取代烯基环硼氮烷的合成路线

Scheme 34. Synthetic routes of asymmetric B-substituted alkenyl borazines

图式35. 乙炔基取代环硼氮烷的合成路线

Scheme 35. Synthesis route of ethynyl-substituted borazine

图式36. B,B',B"-芳基环硼氮烷的合成路线

Scheme 36. Synthesis route of B,B',B"-aryl borazine

图式37. B,B',B"-三甲氧基环硼氮烷的合成路线

Scheme 37. Synthesis route of B,B',B"-trimethoxy borazine

图式38. 环硼氮烷与氯化氢的反应路线

Scheme 38. Synthesis route of borazine with hydrogen chloride

图式39. 环硼氮烷与溴的反应路线

Scheme 39. Synthetic routes of borazine with bromine

图式40. 环硼氮烷与芳香胺的反应路线

Scheme 40. Synthesis route of borazine with aromatic amines

图式41. 二戊胺改性聚环硼氮烷的合成路线

Scheme 41. Synthesis route of dipentylamine-modified polybo- razine

图式42. 环硼氮烷改性氢化聚硅氮烷的合成路线

Scheme 42. Synthesis route of borazine-modified hydrogenated polysilazane

图式43. (a)环硼氮烷与TTS的热缩合反应; (b)环硼氮烷与HCT的热缩合反应

Scheme 43. (a) Thermal condensation reaction of borazine with TTS; (b) Thermal condensation reaction of borazine with HCT

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