技术文章

Tetrahydroxydiboron/Bis-Boric Acid/BBA/B2(OH)4

Sandra Forbes

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Tetrahydroxydiboron is a reducing agent, that for example slowly produces hydrogen gas in water.

 

Recent Literature


A rhodium-catalyzed transfer hydrogenation of functionalized arenes in the presence of tetrahydroxydiboron offers good functional group tolerance, operational simplicity and controllable chemoselectivity. The general applicability of this procedure is demonstrated by the selective hydrogenation of a range of arenes, including functionalized benzenes, biphenyls, and polyaromatics.
Y. Wang, Z. Chang, Y. Hu, X. Lin, X. Dou, Org. Lett., 2021, 23, 1910-1914.

10.1021/acs.orglett.1c00341

 


A metal-free reduction of nitro aromatics is mediated by tetrahydroxydiboron under mild conditions in water as solvent to provide various aromatic amines with good functional group tolerance and in good yields.
D. Chen, Y. Zhou, H. Zhou, S. Liu, Q. Liu, K. Zhang, Y. Uozumi, Synthesis, 2018, 50, 1765-1768.

10.1055/s-0037-1610086

 


The use of tetrahydroxydiboron as reductant and 4,4′-bipyridine as organocatalyst enables a metal-free and highly chemoselective reduction of aromatic nitro compounds within 5 min at room temperature. Under optimal conditions, sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen were tolerated.
M. Jang, T. Lim, B. Y. Park, M. S. Han, J. Org. Chem., 2022, 87, 910-919.

10.1021/acs.joc.1c01431

 


B2(OH)4 mediates a reductive transamidation reaction between N-acyl benzotriazoles and organic nitro compounds or NaNO2 under mild conditions in H2O as solvent. N-Deuterated amides can be synthesized when conducting the reaction in D2O. A reasonable reaction mechanism involves bond metathesis between the AcBt amide and an amino boric acid intermediate.
J. Bai, S. Li, R. Zhu, Y. Li, W. Li, J. Org. Chem., 2023, 88, 3714-3723.

10.1021/acs.joc.2c02995

 


An effient tandem process consisting of palladium-catalyzed double-bond isomerization of long-chain olefins followed by intramolecular cyclization promoted by B2(OH)2 provides benzo-fused oxazaheterocycles. This strategy also provides rapid access to pyrido[3,4-b]indoles, trans-2-olefins, and enamides with high regio- and stereoselectivity.
L. Ding, Y.-N. Niu, X.-F. Xia, J. Org. Chem., 2021, 86, 10032-10042.

10.1021/acs.joc.1c00770

 


A copper-catalyzed one-pot reaction of 2-nitrobenzonitriles and various carbonyl compounds in the presence of diboronic acid as a reductant provides 2,3-dihydroquinazolin-4(1H)-ones with good functional-group tolerance in good yields under mild conditions.
Q. Liu, Y. Sui, Y. Zhang, K. Zhang, Y. Chen, H. Zhou, Synlett, 2020, 31, 275-279.

10.1055/s-0037-1610740

 

Quoted from: https://www.organic-chemistry.org/chemicals/reductions/tetrahydroxydiboron-bba.shtm

 

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Da — 若无特别说明,分子量单位默认为道尔顿。   Mw — 重均分子量。   Mn — 数均分子量。

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阿拉丁科学.《Tetrahydroxydiboron/Bis-Boric Acid/BBA/B2(OH)4》. 阿拉丁知识库,更新于 2024年4月8日。 https://www.aladdin-e.com/zh_cn/faqs/tetrahydroxydiboron-bis-boric-acid-bba-b2-oh-4-en.html
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