22248-26-6Relevant academic research and scientific papers
Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides
Gao, Mengyu,Sun, Deli,Gong, Hegui
supporting information, p. 1645 - 1648 (2019/03/11)
A Ni-catalyzed reductive cross-coupling of α-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes α-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates α-carbonyl radicals.
Selective Palladium-Catalyzed Carbonylation of Alkynes: An Atom-Economic Synthesis of 1,4-Dicarboxylic Acid Diesters
Liu, Jiawang,Dong, Kaiwu,Franke, Robert,Neumann, Helfried,Jackstell, Ralf,Beller, Matthias
supporting information, p. 10282 - 10288 (2018/08/03)
A class of novel diphosphine ligands bearing pyridine substituents was designed and synthesized for the first time. The resulting palladium complexes of L1 allow for chemo- and regioselective dialkoxycarbonylation of various aromatic and aliphatic alkynes affording a wide range of 1,4-dicarboxylic acid diesters in high yields and selectivities. Kinetic studies suggest the generation of 1,4-dicarboxylic acid diesters via cascade hydroesterification of the corresponding alkynes. Based on these investigations, the chemo- and regioselectivities of alkyne carbonylations can be controlled as shown by switching the ligand from L1 to L3 or L9 to give α,β-unsaturated esters.
Co-catalysis over a bi-functional ligand-based Pd-catalyst for tandem bis-alkoxycarbonylation of terminal alkynes
Yang, Da,Liu, Huan,Wang, Dong-Liang,Luo, Zhoujie,Lu, Yong,Xia, Fei,Liu, Ye
, p. 2588 - 2595 (2018/06/11)
A bi-functional ligand (L1) containing a diphosphino fragment and sulfonic acid group (-SO3H) enabled PdCl2(MeCN)2 to efficiently catalyze the tandem bis-alkoxycarbonylation of terminal alkynes to produce aryl-/alkyl-substituted succinate (α,ω-diesters). It was found that the -SO3H incorporated in L1 indispensably assisted the Pd-catalyst in accomplishing this tandem reaction via intramolecular synergic effects. Co-catalysis over the L1-based Pd-catalyst was not due to the physical mixture of Xantphos and MeSO3H. In situ FTIR analysis verified that the formation and stability of Pd-H active species were facilitated by the presence of L1. The formation of stabilized diacylpalladium intermediate (F) was the critical driving force for the second-step methoxycarbonylation. DFT calculation was carried out to optimize the geometric structure of F, which indicated that the developed intramolecular O?H hydrogen bonds were an important structural feature to stabilize F. In addition, the L1-based Pd-catalyst could be recycled successfully for at least 3 runs in the ionic liquid [Bmim]NTf2 without obvious activity loss and detectable metal leaching.
Palladium-catalyzed intermolecular Alkoxy-alkoxycarbonylation of Vinylphenols in the presence of copper salt: Unexpected cooperative effect of tin salt
Phan, Nga Hang Thi,Furuya, Tomoki,Soeta, Takahiro,Ukaji, Yutaka
supporting information, p. 1431 - 1433 (2016/12/03)
Palladium-catalyzed intermolecular alkoxy-alkoxycarbonylation of vinylphenols under normal pressure of CO and O2 in alcohol was developed to afford the corresponding 3-alkoxy-3-arylpropanoates in good to high yields. Not only primary alcohols but also secondary alcohols were applicable to the present reaction. The presence of a tin salt was crucial to realize reproducibly high yields.
Selective aryl α-diimine/palladium-catalyzed bis-alkoxycarbonylation of olefins for the synthesis of substituted succinic diesters
Fini, Francesco,Beltrani, Michela,Mancuso, Raffaella,Gabriele, Bartolo,Carfagna, Carla
, p. 177 - 184 (2015/01/30)
Aryl α-diimine derivatives have been used, for the first time, as efficient new ligands for the palladium-catalyzed oxidative bis-alkoxycarbonylation reaction of olefins. The most active catalyst was formed in situ from bis(9-anthryl)-2,3-dimethyl-1,4-dia
Small molecule inhibitors of plasma kallikrein
Young, Wendy B.,Rai, Roopa,Shrader, William D.,Burgess-Henry, Jana,Hu, Huiyong,Elrod, Kyle C.,Sprengeler, Paul A.,Katz, Bradley A.,Sukbuntherng, Juthamas,Mordenti, Joyce
, p. 2034 - 2036 (2007/10/03)
Plasma kallikrein is a serine protease that is involved in pathways of inflammation, complement fixation, coagulation, and fibrinolysis. Herein, we describe the SAR and structural binding modes of a series of inhibitors of plasma kallikrein as well as the
Factor VIIa inhibitors: Chemical optimization, preclinical pharmacokinetics, pharmacodynamics, and efficacy in an arterial baboon thrombosis model
Young, Wendy B.,Mordenti, Joyce,Torkelson, Steven,Shrader, William D.,Kolesnikov, Aleksandr,Rai, Roopa,Liu, Liang,Hu, Huiyong,Leahy, Ellen M.,Green, Michael J.,Sprengeler, Paul A.,Katz, Bradley A.,Yu, Christine,Janc, James W.,Elrod, Kyle C.,Marzec, Ulla M.,Hanson, Stephen R.
, p. 2037 - 2041 (2007/10/03)
Highly selective and potent factor VIIa-tissue factor (fVIIa · TF) complex inhibitors were generated through structure-based design. The pharmacokinetic properties of an optimized analog (9) were characterized in several preclinical species, demonstrating
Development of Thiourea-Based Ligands for the Palladium-Catalyzed Bis(methoxycarbonylation) of Terminal Olefins
Dai, Mingji,Wang, Cuihua,Dong, Guangbin,Xiang, Jing,Luo, Tuoping,Liang, Bo,Chen, Jiahua,Yang, Zhen
, p. 4346 - 4348 (2007/10/03)
Thiourea-based ligands were evaluated for the palladium-catalyzed bis(methoxycarbonylation) of terminal olefins. The usefulness of these ligands for this reaction is demonstrated by their stability to oxidizing agents, and their superiority in preventing
Phosphine sulfides: Novel effective ligands for the palladium-catalyzed bisalkoxycarbonylation of olefins
Hayashi, Minoru,Takezaki, Hiroshi,Hashimoto, Yukihiko,Takaoki, Kazuo,Saigo, Kazuhiko
, p. 7529 - 7532 (2007/10/03)
Phosphine sulfides were found to be effective as a ligand in the palladium(II)-catalyzed bisalkoxycarbonylation of olefins. Aromatic olefins and vinylsilanes were converted into the corresponding succinates in high yields under mild conditions. Enantiosel
