Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond

doi:10.6023/cjoc202211040

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (3): 1045-1068.DOI: 10.6023/cjoc202211040 Previous Articles Next Articles

Special Issue: 中国女科学家专辑

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过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展

贾海瑞^a^,^b, 邱早早^b^,^c^,^d^,^*()

a 上海理工大学材料与化学学院上海 200093
b 中国科学院上海有机化学研究所沪港化学合成联合实验室上海 200032
c 中国科学院大学杭州高等研究院化学与材料科学学院杭州 310024
d 中国科学院上海有机化学研究所能量调控材料重点实验室上海 200032

收稿日期:2022-11-30 修回日期:2022-12-23 发布日期:2023-01-05
通讯作者: 邱早早
基金资助:
国家自然科学基金(92056106); 中国科学院沪港化学合成联合实验室资助项目

Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond

Hairui Jia^a^,^b, Zaozao Qiu^b^,^c^,^d()

a School of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093
b Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
d CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-11-30 Revised:2022-12-23 Published:2023-01-05
Contact: Zaozao Qiu
Supported by:
National Natural Science Foundation of China(92056106); Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Chinese Academy of Sciences

Carboranes are a class of carbon-boron molecular clusters with exceptional thermal and chemical stabilities. They are finding a variety of applications in medicine, materials, and coordination/organometallic chemistry as functional building blocks. Recently, transition metal catalyzed regioselective o-carborane B—H activation has been rapidly developed, offering a series of novel methodologies for selective cage boron functionalization. The current state of functionalization of o-carboranes to form B—B, B—N, B—O, B—S, and B—halogen bonds using transition metal-catalyzed B—H activation strategy is summarized. Some reaction mechanisms are highlighted, and the future challenges and focus of the carborane B—heteroatom bond construction are discussed.

Key words: carborane, B—H activation, transition metal catalysis, B—heteroatom bond

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Hairui Jia, Zaozao Qiu. Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond[J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1045-1068.

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Fig. & Tab. 35

Scheme 1. Synthetic approaches to construct B—heteroatom bond of o-carboranes

Scheme 2. Ir-catalyzed B(3,6)-diborylation or B(3)-borylation

Scheme 3. Ir-catalyzed B(4)-borylation

Scheme 4. Pd-catalyzed synthesis of bis-o-carboranes

Scheme 5. Ru-catalyzed B(4)-amination with sulfonyl azides

Scheme 6. Ir-catalyzed B(4)-amination with azides

Scheme 7. Pd-catalyzed B(4)-amination with O-benzoyl hydroxylamines

Scheme 8. Rh-catalyzed B(4)-amination with dioxazolones

Scheme 9. Ir-catalyzed B(4)-amination with dioxazolones

Scheme 10. Ir-catalyzed B(4)-amination with 2,1-benzisoxazoles

Scheme 11. Ir-catalyzed B(4)-amination with primaryamine

Scheme 12. Ir-catalyzed cascade B(4)-arylation and B(5)-amination with benzamides

Scheme 13. One-pot B(3)-alkenylation and B(4)-amidination via Pd-migration

Scheme 14. One-pot B(3)-alkenylation and B(4)-amination via Pd-migration

Scheme 15. Ir-catalyzed B(3)-amination with ammonia gas

Scheme 16. Rh-catalyzed B(3)-amination with sulfonyl amides

Scheme 17. Pd-catalyzed B(9)-amination with O-benzoyl hydroxylamines

Scheme 18. Pd-catalyzed B(9)-amination with acidic nitrogen sources

Scheme 19. Rh-catalyzed B(4)-hydroxylation with O2

Scheme 20. Pd-catalyzed B(4)-acyloxylation with phenyliodonium dicarboxylates

Scheme 21. Ir-catalyzed cascade B(4)-arylation and B(5)-amination with benzoic acids

Scheme 22. Cu-catalyzed electrochemical selective B(4)-oxygenation or B(4,5)-dioxygenation

Scheme 23. Cu-catalyzed B(4,5)-disulfenylation with disulfides

Scheme 24. One-pot construction of B—C and B—O/S bonds via Pd-migration

Scheme 25. Rh-catalyzed cascade B(3,4,5)-trifunctionalization with diarylalkynes and copper salts

Scheme 26. Rh-catalyzed B(3)-acyloxylation with carboxylic acids

Scheme 27. Pd-catalyzed B(3)- and B(3,4)-acyloxylation with carboxylic acids

Scheme 28. Pd-catalyzed intramolecular dehydrogenative coupling of B(3/4)—H and O—H

Scheme 29. Pd-catalyzed B(8,9,10,12)-tetraacyloxylation and B(8/9)-acyloxylation with PhI(OAc)2

Scheme 30. Ir-catalyzed B(4)-halogenation

Scheme 31. Pd-catalyzed B(4,5)-iodination with IOAc

Scheme 32. Pd-catalyzed B(4,7,8)-triflorination with 1-fluoro- pyridinium tetrafluoroborate

Scheme 33. Pd-catalyzed B(3)-halogination with aryl halides

Scheme 34. Pd-catalyzed B(8,9,10,12)-tetraflorination with 1- fluoropyridinium trifluoromethanesulfate

Scheme 35. Pd-catalyzed B(8/9)-chlorination with FeCl3

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过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展

Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond

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