Recent Advances in the Synthesis and Functionalization of Borazine and Its Derivatives

doi:10.6023/cjoc202605024

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (9): 3372-3389.DOI: 10.6023/cjoc202605024 Previous Articles Next Articles

REVIEW

环硼氮烷及其衍生物的合成与官能团化研究进展

冯嘉婷^†, 王梓宇^†, 付雪薇, 王柏文, 江焕峰^*()

华南理工大学化学与化工学院广东省功能分子工程重点实验室广州 510641

收稿日期:2026-05-24 修回日期:2026-07-01 发布日期:2026-07-23
通讯作者: 江焕峰
作者简介:
^† 共同第一作者
基金资助:
国家自然科学基金(22231002); 国家自然科学基金(22571094)

Recent Advances in the Synthesis and Functionalization of Borazine and Its Derivatives

Jiating Feng, Ziyu Wang, Xuewei Fu, Bowen Wang, Huanfeng Jiang^*()

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641

Received:2026-05-24 Revised:2026-07-01 Published:2026-07-23
Contact: Huanfeng Jiang
About author:
Dedicated to the 100th anniversary of the birth of Professor Xikui Jiang.
^† These authors contributed equally to this work
Supported by:
National Natural Science Foundation of China(22231002); National Natural Science Foundation of China(22571094)

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

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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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Fig. & Tab. 45

Figure 1. Structures of borazine and benzene

Scheme 1. Stockʼs synthetic route to borazine

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

Scheme 3. Formation of borazine from pyrolysis of ammonia borane

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

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

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

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

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

Scheme 9. Synthesis and polymerization of 19

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

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

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

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

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

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

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

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

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

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

Scheme 19. Synthesis of 59

Scheme 20. Bromination of terphenylborazine

Scheme 21. Reaction process of BCl3 with amines

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

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

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

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

Scheme 26. Synthetic route of 87

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

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]

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

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

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

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

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

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

Scheme 35. Synthesis route of ethynyl-substituted borazine

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

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

Scheme 38. Synthesis route of borazine with hydrogen chloride

Scheme 39. Synthetic routes of borazine with bromine

Scheme 40. Synthesis route of borazine with aromatic amines

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

Scheme 42. Synthesis route of borazine-modified hydrogenated polysilazane

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

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环硼氮烷及其衍生物的合成与官能团化研究进展

Recent Advances in the Synthesis and Functionalization of Borazine and Its Derivatives

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