898767-06-1Relevant academic research and scientific papers
Syntheses of Pyrroles, Pyridines, and Ketonitriles via Catalytic Carbopalladation of Dinitriles
Qi, Linjun,Li, Renhao,Yao, Xinrong,Zhen, Qianqian,Ye, Pengqing,Shao, Yinlin,Chen, Jiuxi
, p. 1097 - 1108 (2020/01/22)
The first example of the Pd-catalyzed addition of organoboron reagents to dinitriles, as an efficient means of preparing 2,5-diarylpyrroles and 2,6-diarylpyridines, has been discussed here. Furthermore, the highly selective carbopalladation of dinitriles with organoboron reagents to give long-chain ketonitriles has been developed as well. Based on the broad scope of substrates, excellent functional group tolerance, and use of commercially available substrates, the Pd-catalyzed addition reaction of arylboronic acid and dinitriles is expected to be significant in future synthetic procedures.
Palladium-Catalyzed Cascade Reactions of I-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines
Chen, Jiuxi,Hu, Maolin,Li, Renhao,Liu, Jichao,Qi, Linjun,Shao, Yinlin,Yao, Xinrong,Zhao, Zhiwei,Zhen, Qianqian
supporting information, p. 114 - 119 (2020/03/25)
This study presents the first example of the Pd-catalyzed cascade reactions of 5-oxohexanenitrile with arylboronic acids, affording important synthon 2-methylpyridines that can be further translated through C(sp3)-H functionalization to construct pyridine derivatives. Furthermore, this chemistry allows 5-oxo-5-Arylpentanenitrile to react with arylboronic acids to provide unsymmetrical 2,6-diarylpyridines. This protocol paves the way for the practical and atom economical syntheses of valuable pyridines with broad functional groups in moderate to excellent yields under mild conditions.
Nickel-Catalyzed Reductive Electrophilic Ring Opening of Cycloketone Oxime Esters with Aroyl Chlorides
Ding, Decai,Wang, Chuan
, p. 11324 - 11329 (2019/01/03)
By merging cross-electrophile coupling and C-C bond cleavage, we developed a Ni-catalyzed electrophilic ring opening of cycloketone oxime esters with aromatic acid chlorides in assistance of Mn as reductant. Notably, complete regioselectivity can be achieved in this C-C bond cleavage reaction, providing an efficient access to a variety of cyanoketones under cyanide-free conditions. A radical reaction pathway was proposed on the basis of the results of the mechanistic probing experiments.
Photoinduced C—C Bond Cleavage and Oxidation of Cycloketoxime Esters
Zhao, Binlin,Tan, Hui,Chen, Cheng,Jiao, Ning,Shi, Zhuangzhi
, p. 995 - 999 (2018/09/25)
A novel structural reorganization of cycloketoxime esters beyond the traditional Beckmann rearrangement process has been established to build cyano-containing ketones in the presence of photocatalyst. This novel transformation is remarkable with selective C—C bond cleavage and an oxidation process enabled by DMSO used as the solvent, oxidant, and oxygen source avoiding acid, base and toxic cyanide salts as the cyano source. Further applications in late-stage modification of complex and chiral molecules have also been reported.
C-C Bond-Forming Strategy by Manganese-Catalyzed Oxidative Ring-Opening Cyanation and Ethynylation of Cyclobutanol Derivatives
Ren, Rongguo,Wu, Zhen,Xu, Yan,Zhu, Chen
supporting information, p. 2866 - 2869 (2016/02/27)
A novel C-C bond-forming strategy employing manganese-catalyzed ring-opening of cyclobutanol substrates, followed by cyanation or ethynylation, is described. A cyano C1 unit and ethynyl C2 unit are regiospecifically introduced to the γ-position of ketones at room temperature, providing a mild yet powerful method for production of elusive aliphatic nitriles and alkynes. All transformations described are based on a common sequence: 1) oxidative ring-opening of cyclobutanol substrates by C-C bond cleavage; 2) radical addition to triple bonds bearing an arylsulfonyl group; and 3) radical-mediated C-S bond cleavage.
Enantioselective titanium(III)-catalyzed reductive cyclization of ketonitriles
Streuff, Jan,Feurer, Markus,Bichovski, Plamen,Frey, Georg,Gellrich, Urs
, p. 8661 - 8664 (2012/09/21)
Reduction, please! The title reaction affords ?-hydroxyketones, a common structural motif in biologically active natural products, in good yields and high enantioselectivities at room temperature. The commercially available ansa-titanocene 1 was found to be an efficient catalyst for this process, which presumably proceeds by addition of a ketyl radical to a nitrile.
Substituted tetrahydrofuroyl-1-phenylalanine derivatives as potent and specific VLA-4 antagonists
Doherty, George A.,Yang, Ginger X.,Borges, Edite,Chang, Linda L.,MacCoss, Malcolm,Tong, Sharon,Kidambi, Usha,Egger, Linda A.,McCauley, Ermenegilda,Van Riper, Gail,Mumford, Richard A.,Schmidt, John A.,Hagmann, William K.
, p. 1501 - 1505 (2007/10/03)
A series of substituted tetrahydrofuroyl-1-phenylalanine derivatives was prepared and evaluated as VLA-4 antagonists. Substitution of the α carbon of the tetrahydrofuran with aryl groups increased the specificity for VLA-4 versus α4β7 while amide substitution increased the potency of the series without increasing the specificity. Substitution of the β carbon of the tetrahydrofuran with keto or amino groups slightly improved the specificity for VLA-4 versus α4β7 but with a significant loss in binding affinity for VLA-4.
