14990-09-1Relevant articles and documents
New N-pyrazole, P-phosphine hybrid ligands and their reactivity towards Pd(II): X-ray crystal structures of complexes with [PdCl2(N,P)] core
Guerrero, Miguel,Mu?oz, Sergio,Ros, Josep,Calvet, Teresa,Font-Bardía, Mercè,Pons, Josefina
, p. 257 - 264 (2015)
Two new N-pyrazole, P-phosphine hybrids ligands: 1-[2-(diphenylphosphanyl)methyl]-3,5-dimethylpyrazole (LP1) and 1-[2-(diphenylphosphanyl)propyl]-3,5-dimethylpyrazole (LP3) are presented. The reaction of these two ligands and two other ligands reported in
Diastereoselective Synthesis of Highly Substituted, Amino- and Pyrrolidino-Tetrahydrofurans as Lead-Like Molecular Scaffolds
Wales, Steven M.,Merisor, Elena G.,Adcock, Holly V.,Pearce, Christopher A.,Strutt, Ian R.,Lewis, William,Hamza, Daniel,Moody, Christopher J.
, p. 8233 - 8239 (2018)
A series of highly substituted tetrahydrofurans (THFs), decorated with modifiable 2-aryl, 3-carboxy and 4-amino substituents, has been prepared for biological evaluation within the European Lead Factory. Diastereoselective reductive amination of pre-functionalised 4-oxofurans, readily prepared from cinnamate esters via oxa-Michael/Dieckmann annulation, provided the requisite THF cores on gram scale with three contiguous stereocentres, including full substitution at C-3. In a second series, a pyrrolidine ring was fused to the same oxofuran scaffold via an intramolecular reductive amination, inverting the configuration at C-4 relative to the other ring substituents. The resulting compounds, which displayed desirable physical properties as lead-like scaffolds, were derivatised into a small library of 24 compounds, demonstrating their ability to serve as starting points for drug discovery. Ultimately, this chemistry enabled the preparation of 1948 THF-containing compounds for inclusion in the Joint European Compound Library.
Palladium supported on polyether-functionalized mesoporous silica. Synthesis and application as catalyst for Heck coupling reaction
Grandsirea, Anne Flore,Labordeb, Coralie,Lamaty, Frederic,Mehdia, Ahmad
, p. 179 - 183 (2010)
A new catalytic system based on Pd supported on polyether-functionalized mesoporous silica was prepared. This material was obtained by co-hydrolysis and polycondensation of tetraethylorthosilicate and a bis-silylated triblock copolymer P123 (Mw = 5800) followed by the decomposition of Pd(OAc)2 salt. We have shown that this material can be applied as powerful heterogeneous catalyst for the Heck coupling reaction. Copyright
Solvent-controlled selective synthesis of a trans-configured benzimidazoline-2-ylidene palladium(II) complex and investigations of its Heck-type catalytic activity
Huynh, Han Vinh,Ho, Joanne Hui Hui,Neo, Tiong Cheng,Koh, Lip Lin
, p. 3854 - 3860 (2005)
Reaction of N,N′-dimethylbenzimidazolyl iodide (A) with Pd(OAc) 2 in DMSO gives selectively trans-bis(N,N′- dimethylbenzimidazoline-2-ylidene) palladium(II) diiodide (trans-2) in 77% yield. The selective formation of the trans-coordination isom
Microwave-assisted copper-catalyzed heck reaction in PEG solvent
Declerck, Valérie,Martinez, Jean,Lamaty, Frédéric
, p. 3029 - 3032 (2006)
A catalytic system made of a copper salt, potassium carbonate and PEG 3400 was developed to perform a Heck arylation under microwave activation. Copper iodide gave the best results in a short reaction time (30 min) and various substituted tert-butyl cinna
Effect of N1-substituted pyrazolic hybrid ligands on palladium catalysts for the Heck reaction
Guerrero, Miguel,Pons, Josefina,Ros, Josep
, p. 1957 - 1960 (2010)
In this paper we have explored the influence of several linkers present on the [PdCl2(L)] complexes, where L is 3,5-dimethylpyrazolic hybrid ligand N1-substituted by polyether chains and/or phenyl groups. These complexes have been used as pre-c
The effect of high pressure on the heck reaction - A contribution to a deeper understanding of the mechanism
Buback, Michael,Perkovic, Thomas,Redlich, Stefan,De Meijere, Armin
, p. 2375 - 2382 (2003)
The influence of high pressure on the Heck reactions of iodobenzene with methyl, ethyl and tert-butyl acrylate, and of both 4-nitrophenyl iodide and 4-nitrophenyl triflate with methyl acrylate, has been studied for the first time by quantitative on-line F
Heteroleptic copper(I) complexes as energy transfer photocatalysts for the intermolecular [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides
Wu, Qing-An,Ren, Chen-Chao,Chen, Feng,Wang, Tian-Qi,Zhang, Yu,Liu, Xue-Fen,Chen, Jian-Bin,Luo, Shu-Ping
supporting information, (2021/05/10)
The [2 + 2] photodimerization of chalcones, cinnamates and cinnamamides can be effectively catalyzed by heteroleptic copper(I) complexes. The reactions were carried out under mild reaction conditions and the products were obtained in 20–72% yield under visible light irradiation. The copper-based photocatalyst comprised of the rigid phenanthroline ligand with substituents at the 2,9-positions and the 4,7-positions showed high activity in the photodimerization via an energy transfer pathway.
Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides
Liu, Xin,Werner, Thomas
, p. 1096 - 1104 (2020/12/31)
Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).
