- Method for preparation of gem-diboron compound by olefin selective 1, 1-diboronation
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The invention relates to a method for preparation of a gem-diboron compound by olefin selective 1, 1-diboronation. The method includes: dissolving an olefin compound, a cyclopentadienyl early transition metal catalyst and an alkali compound in a solvent, then adding a borane compound, carrying out reaction at 60-150DEG C for 1-16h in a protective atmosphere, and then carrying out separation to obtain the gem-diboron compound. The method is simple and convenient to operate, low in cost, and high in reaction atom economy, and is suitable for industrial production.
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Paragraph 0069-0070
(2020/06/17)
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- Zirconium-Catalyzed Atom-Economical Synthesis of 1,1-Diborylalkanes from Terminal and Internal Alkenes
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A general and atom-economical synthesis of 1,1-diborylalkanes from alkenes and a borane without the need for an additional H2 acceptor is reported for the first time. The key to our success is the use of an earth-abundant zirconium-based catalyst, which allows a balance of self-contradictory reactivities (dehydrogenative boration and hydroboration) to be achieved. Our method avoids using an excess amount of another alkene as an H2 acceptor, which was required in other reported systems. Furthermore, substrates such as simple long-chain aliphatic alkenes that did not react before also underwent 1,1-diboration in our system. Significantly, the unprecedented 1,1-diboration of internal alkenes enabled the preparation of 1,1-diborylalkanes.
- Cui, Xin,Jiao, Haijun,Li, Sida,Wang, Xianjin,Wang, Yue,Wu, Lipeng,Xia, Chungu
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supporting information
p. 13608 - 13612
(2020/06/02)
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- Preparation method and application of geminal diboron compound
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The invention discloses a preparation method and application of a geminal diboron compound. The preparation method includes: in a protective atmosphere, subjecting a uniform mixture system of a carbonyl compound, a diboron reagent, an iron catalyst, an alkaline substance, a proton source and a solvent to reaction at 60-150 DEG C for 3-36 h, and separating to obtain the geminal diboron compound. The preparation method herein constructs, in one step, the geminal diboron compound which is difficult to efficiently implement in the past, from simple, economical and easily accessible materials as substrates under catalyst of the iron catalyst; the geminal diboron compound has a good application prospect in the sciences of pharmaceutical synthetic intermediates and organic photoelectric materials; the preparation method herein helps solve the problem that the field of traditional preparation of geminal diboron compounds requires pre-functionalization or some substrates are incompatible; the reaction conditions are relatively mild; operation is simple; the raw materials are economical and easy to attain; the reaction efficiency is high; the preparation method herein provides good functional group compatibility.
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Paragraph 0040; 0041; 0042; 0044; 0045; 0046
(2019/05/22)
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- A modular and concise approach to MIDA acylboronates: Via chemoselective oxidation of unsymmetrical geminal diborylalkanes: Unlocking access to a novel class of acylborons
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Acylboronates represent a very intriguing and rare class of organoboronates. Synthesis of these compounds from readily available substrates under mild conditions and access to novel classes of acylborons has been challenging. We report a novel and concise route to various MIDA acylboronates from terminal alkynes/alkenes or vinyl boronic esters using unsymmetrical geminal diborylalkanes as key intermediates. The high modularity and mild conditions of this strategy allowed a facile access to acylboronates possessing aliphatic, aromatic as well as the rarer heteroaromatic, alkynyl and α,β-unsaturated scaffolds. To the best of our knowledge, this is the first report of chemoselective oxidation of geminal diborons as well as synthesis of an α,β-unsaturated acylboronate.
- Lin, Shengjia,Wang, Lucia,Aminoleslami, Negin,Lao, Yanting,Yagel, Chelsea,Sharma, Abhishek
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p. 4684 - 4691
(2019/05/14)
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- Synthesis of 1,1-organodiboronates via Rh(I)CI-catalyzed sequential regioselective hydroboration of 1-alkynes
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A Rh(I)Cl-DPPB-complex-catalyzed sequential hydroboration of aryl alkynes and aliphatic alkynes was achieved. The reaction proceeded with almost perfect regioselectivity to afford 1,1-organodiboronate compounds in moderate to good yield. Georg Thieme Verl
- Endo, Kohei,Hirokami, Munenao,Shibata, Takanori
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experimental part
p. 1331 - 1335
(2009/10/23)
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