7302-06-9Relevant academic research and scientific papers
Nickel-Catalyzed Arylation of C(sp3)-O Bonds in Allylic Alkyl Ethers with Organoboron Compounds
Li, Xiaowei,Li, Yuxiu,Zhang, Zhong,Shi, Xiaolin,Liu, Ruihua,Wang, Zemin,Li, Xiangqian,Shi, Dayong
supporting information, p. 6612 - 6616 (2021/09/02)
A nickel-catalyzed cross-coupling of allylic alkyl ethers with organoboron compounds through the cleavage of the inert C(sp3)-O(alkyl) bonds is described. Several types of allylic alkyl ethers can be coupled with various boronic acids or their derivatives to give the corresponding products in good to excellent yields with wide functional group tolerance and excellent regioselectivity. The gram-scale reaction and late-stage modification of biologically active compounds further prove the practicality of this synthetic method.
Bis-quinoline-2-carboxylic acid Copper Salt as an Efficient Catalyst for Synthesis of Aryl Olefins by Heck Reaction
Zuo, Minghui,Li, Zhuofei,Fu, Wanyong,Guo, Rui,Hou, Chuanfu,Guo, Weihao,Sun, Zhizhong,Chu, Wenyi
, p. 3217 - 3223 (2019/07/17)
Abstract: A bis-quinoline-2-carboxylic acid copper salt as a single crystal was prepared and characterized by X-ray single crystal analysis. The crystal as a catalyst was applied to the Mizoroki–Heck coupling reaction between arylboronic acids and α-olefins. A series of diarylethenes and aryl olefins were synthesized with good to excellent yields at room temperature. The catalytic system exhibited good functional group tolerance and low pollution. Graphic Abstract: A bis-quinoline-2-carboxylic acid copper salt as a single crystal was prepared and characterized by X-ray single crystal analysis. The crystal as a catalyst was applied to the Mizoroki–Heck coupling reaction between arylboronic acids and α-olefins[InlineMediaObject not available: see fulltext.].
Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
Wang, Gaonan,Gan, Yi,Liu, Yuanhong
supporting information, p. 916 - 920 (2018/09/22)
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.
Iron-Catalyzed Remote Arylation of Aliphatic C-H Bond via 1,5-Hydrogen Shift
Zhou, Bingwei,Sato, Hiroki,Ilies, Laurean,Nakamura, Eiichi
, p. 8 - 11 (2018/01/17)
Catalytic amounts of an iron(III) salt and a N-heterocyclic carbene ligand catalyze the arylation of 2-iodoalkylarenes with diphenylzinc selectively at the C-H bond of the alkyl side chain. Several lines of evidence suggest that the iron catalyst reacts with the aryl iodide moiety of the substrate to generate an aryliron intermediate that behaves in a radical manner and cleaves the aliphatic C-H bond through 1,5-hydrogen transfer; the resulting alkyliron intermediate undergoes reductive elimination to give the arylated product.
Chemo- and regioselective reductive deoxygenation of 1-en-4-yn-ols into 1,4-enynes through FeF3 and TfOH co-catalysis
Yang, Zonglian,Kumar, Rapolu Kiran,Liao, Peiqiu,Liu, Zhaohong,Li, Xingqi,Bi, Xihe
supporting information, p. 5936 - 5939 (2016/05/24)
We report chemo- and regioselective direct reductive deoxygenation of 1-en-4-yn-3-ols into 1,4-enynes through FeF3 and TfOH cooperative catalysis under NBSH-mediated conditions. Further, we show the efficient synthesis of a pharmaceutically significant 1,4-enyne. The present methodology can also be used for chemo- and regioselective direct deoxygenation of other alcohols.
Cross-coupling of N-allylic sulfonimides with organozinc reagents at room temperature
Tang, Xiang-Ling,Wu, Zhao,Li, Man-Bo,Gu, Yonghong,Tian, Shi-Kai
, p. 4107 - 4109 (2012/09/08)
An efficient cross-coupling reaction of N-allylic sulfonimides with organozinc reagents has been developed. In the presence of 1 mol-% of Pd 2(dba)3, a range of N-allylic sulfonimides smoothly couple with various organozinc reagents at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive α-selectivity. It is noteworthy that allyl ether, benzyl ether, and ester are tolerated under the reaction conditions. A range of N-allylic sulfonimides smoothly couple with various organozinc reagents in the presence of 1 mol-% of Pd2(dba)3 at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive α-selectivity.
Regioselective and stereospecific cross-coupling of primary allylic amines with boronic acids and boronates through palladium-catalyzed C-N bond cleavage
Li, Man-Bo,Wang, Yong,Tian, Shi-Kai
supporting information; experimental part, p. 2968 - 2971 (2012/04/18)
The NH2 group serves as an effective leaving group in the palladium-catalyzed regioselective and stereospecific title reaction (see scheme). The reaction works well with aryl- and alkenylboronic acids and aryl-, alkenyl-, allyl-, and benzylboronates, and complete transfer of chirality has been achieved when using α-chiral primary allylic amines as the allylic electrophiles. Copyright
Cobalt-catalyzed benzylzincation of alkynes
Murakami, Kei,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 7688 - 7691 (2010/09/10)
Chemical Equotion Present Carbometalation: Cobalt salts catalyze benzylzincation of alkynes to afford benzylated multisubstituted alkenes with high regio- and stereoselectivity. The scope of the reaction is wide enough to apply unfunctionalized alkynes as well as arylacetylenes. The reaction offers a new route to the regio- and stereoselective synthesis of an estrogen receptor antagonist (see scheme).
A versatile catalyst system for suzuki-miyaura cross-coupling reactions of C(sp2)-tosylates and mesylates
Bhayana, Brijesh,Fors, Brett P.,Buchwald, Stephen L.
supporting information; experimental part, p. 3954 - 3957 (2009/12/03)
Figure Presented A catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl and vinyl tosylates and mesylates has been developed. This catalyst displays excellent functional group tolerance and allows the coupling of heteroarylboronic acids
Palladium(0)-catalyzed direct cross-coupling reaction of allylic alcohols with aryl- and alkenylboronic acids
Tsukamoto, Hirokazu,Uchiyama, Tomomi,Suzuki, Takamichi,Kondo, Yoshinori
supporting information; experimental part, p. 3005 - 3013 (2009/02/03)
Allylic alcohols can be used directly for the palladium(0)-catalyzed allylation of aryl- and alkenylboronic acids with a wide variety of functional groups. A triphenylphosphine-ligated palladium catalyst turns out to be most effective for the cross-coupling reaction and its low loading (less than 1 mol%) leads to formation of the coupling product in high yield. The Lewis acidity of the organoboron reagents and poor leaving ability (high basicity) of the hydroxyl group are essential for the cross-coupling reaction. The reaction process is atom-economical and environmentally benign, because it needs neither preparation of allyl halides and esters nor addition of stoichiometric amounts of a base. Furthermore, allylic alcohols containing another unsaturated carbon-carbon bond undergo arylative cyclization reactions leading to cyclopentane formation. The Royal Society of Chemistry.
