19396-72-6Relevant articles and documents
Zirconium-Catalyzed Atom-Economical Synthesis of 1,1-Diborylalkanes from Terminal and Internal Alkenes
Cui, Xin,Jiao, Haijun,Li, Sida,Wang, Xianjin,Wang, Yue,Wu, Lipeng,Xia, Chungu
, p. 13608 - 13612 (2020/06/02)
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.
Method for preparing alcohol through reaction of Suzuki no exogenous alkali (by machine translation)
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Paragraph 0022-0026; 0042-0044, (2020/02/14)
The method for synthesizing the alcohol compound by. using the method disclosed by the invention for preparing .the alcohol compound by adopting the method Suzuki disclosed by the invention has the advantages that the reaction system, is convenient and convenient, to prepare, and the reaction system is convenient to prepare . Suzuki. (by machine translation)
Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes
Logan, Kaitlyn M.,Sardini, Stephen R.,White, Sean D.,Brown, M. Kevin
supporting information, p. 159 - 162 (2018/01/17)
A Ni-catalyzed method for arylboration is disclosed. The method allows for highly stereoselective arylboration of unactivated alkenes. The reactions utilize a simple Ni-catalyst and work with a broad range of alkenes and aryl bromides. The products represent useful intermediates for chemical synthesis due to the versatility of the C-B bond. Preliminary mechanistic details of the method are also disclosed.
Hydroxyl-Directed Cross-Coupling: A Scalable Synthesis of Debromohamigeran e and Other Targets of Interest
Blaisdell, Thomas P.,Morken, James P.
supporting information, p. 8712 - 8715 (2015/07/27)
A hydroxyl functional group positioned β to a pinacol boronate can serve to direct palladium-catalyzed cross-coupling reactions. This feature can be used to control the reaction site in multiply borylated substrates and can activate boronates for reaction that would otherwise be unreactive.
Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds
Lu, Xiao-Yu,Yang, Chu-Ting,Liu, Jing-Hui,Zhang, Zheng-Qi,Lu, Xi,Lou, Xin,Xiao, Bin,Fu, Yao
supporting information, p. 2388 - 2391 (2015/02/05)
A copper-catalyzed cross-coupling reaction of epoxides with arylboronates is described. This reaction is not limited to aromatic epoxides, because aliphatic epoxides are also suitable substrates. In addition, N-sulfonyl aziridines can be successfully converted into the products. This reaction provides convenient access to β-phenethyl alcohols, which are valuable synthetic intermediates.
Nickel-catalyzed regiodivergent opening of epoxides with aryl halides: Co-catalysis controls regioselectivity
Zhao, Yang,Weix, Daniel J.
supporting information, p. 48 - 51 (2014/01/23)
Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis results in opening at the less hindered position via an iodohydrin intermediate. Titanocene cocatalysis results in opening at the more hindered position, presumably via TiIII-mediated radical generation. 1,2-Disubstituted epoxides are opened under both conditions to form predominantly the trans product.
A simple and inexpensive procedure for low valent copper mediated benzylation of aldehydes in wet medium
Dubey, Akhil Kr.,Goswami, Dibakar,Chattopadhyay, Angshuman
experimental part, p. 137 - 145 (2010/10/02)
An operationally simple, inexpensive and efficient procedure for benzylation of aldehydes in wet medium has been developed that was mediated with low valent copper, prepared in situ through spontaneous reduction of CuCl 2-2H2O with magnesium in situ. Notably, copper mediated benzylation of 3h took place with good syn selectivity that was opposite to that for the corresponding Grignard addition. Finally, homobenzyl alcohol 5a was elegantly transformed into a known protease inhibitor synthon I. ARKAT USA, Inc.
Arylsilanes: Application to gold-catalyzed oxyarylation of alkenes
Ball, Liam T.,Green, Michael,Lloyd-Jones, Guy C.,Russell, Christopher A.
supporting information; experimental part, p. 4724 - 4727 (2010/12/25)
Arylsilanes are efficient reagents for the gold-catalyzed oxyarylation of alkenes (21 examples, up to 85% isolated yield). Using commercially available Ph3PAuCl and readily prepared, benign arylsilanes, these two- and three-component reactions
Gold-catalyzed three-component coupling: Oxidative oxyarylation of alkenes
Melhado, Asa D.,Brenzovich Jr., William E.,Lackner, Aaron D.,Toste, F. Dean
supporting information; experimental part, p. 8885 - 8887 (2010/08/21)
The three-component coupling of terminal alkenes with arylboronic acids and oxygen nucleophiles is described. The reaction employs a binuclear gold(I) bromide as a catalyst and Selectfluor reagent as the stoichiometric oxidant. Alcohols, carboxylic acids, and water can be employed as oxygen nucleophiles, thus providing an efficient entry into β-aryl ethers, esters, and alcohols from alkenes.
Cadmium-mediated carbonyl benzylation in tap water
Zhou, Cunliu,Wang, Zhiyong
, p. 1649 - 1655 (2007/10/03)
Zn/CdCl2 has been developed as a mediator in the benzylation of various aldehydes in tap water affording the corresponding alcohols in moderate to good yields. The addition of a catalytic amount of InCl3 increases the yield of benzylation product significantly. It can selectively mediate the benzylation of aldehydes in the presence of ketones. A mechanism involving the formation of a cation π-complex is proposed based on the experimental facts. Georg Thieme Verlag Stuttgart.