1136-24-9Relevant academic research and scientific papers
Synergistic effect of a bis(proazaphosphatrane) in mild palladium-catalyzed direct α-arylations of nitriles with aryl chlorides
Han Kim, So,Jang, Wonseok,Kim, Min,Verkade, John G.,Kim, Youngjo
, p. 6025 - 6029 (2015/03/30)
The effect of a bis(proazaphosphatrane) ligand on the palladium-catalyzed direct α-arylation of nitriles with various aryl chlorides under mild conditions is reported. Comparisons of the catalytic properties of this ligand with those of three related mono(proazaphosphatrane)s under the same reaction conditions revealed that bis(proazaphosphatrane) displayed a synergistically enhanced activity. In the presence of the bis(proazaphosphatrane) ligand, ethyl cyanoacetate and primary as well as secondary nitriles were efficiently coupled with a wide variety of aryl chlorides that contained electron-rich, electron-poor, and electron-neutral groups.
An efficient method for the preparation of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC)
Behera, Manoranjan,Venkat Ragavan,Sambaiah,Erugu, Balaiah,Rama Krishna Reddy,Mukkanti,Yennam, Satyanarayana
experimental part, p. 1060 - 1062 (2012/03/26)
An efficient method for the synthesis of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC) has been described. Using this method many sterically hindered and highly substituted mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate were synthesized in high yield.
Palladium-catalyzed one-pot synthesis of 2-alkyl-2-arylcyanoacetates
Wang, Xiang,Guram, Anil,Bunel, Emilio,Cao, Guo-Qiang,Allen, Jennifer R.,Faul, Margaret M.
, p. 1643 - 1645 (2008/09/17)
(Chemical Equation Presented) A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a Pd(OAc)2/DPPF (DPPF = 1,1′-diphenylphosphino ferreocene)-catalyzed enolate arylation followed by in situ alkylation has been developed. This procedure tolerates a diverse range of aryl and heteroaryl bromides, and provides a rapid entry to a variety of 2-alkyl-2-arylcyanoacetates in good to excellent yield.
An efficient and mild CuI/L-proline-catalyzed arylation of acetylacetone or ethyl cyanoacetate
Jiang, Yongwen,Wu, Nan,Wu, Haihong,He, Mingyuan
, p. 2731 - 2734 (2007/10/03)
The coupling reaction of aryl iodides with acetylacetone or ethyl cyanoacetate under catalysis of CuI/L-proline works at relatively mild conditions to provide 3-aryl-2, 4-pentanediones and α-aryl cyanoacetates in moderate to good yields. Georg Thieme Verlag Stuttgart.
A General Method for the Direct α-Arylation of Nitriles with Aryl Chlorides
You, Jingsong,Verkade, John G.
, p. 5051 - 5053 (2007/10/03)
The long-standing challenge of developing a general method for the title methodology is met for a broad range of aryl chlorides through the use of bicyclic P(iBuNCH2CH2)3N (1) as a bulky electron-rich ligand for palladium (see scheme, dba = dibenzylideneacetone).
P(i-BuNCH2CH2)3N: An efficient ligand for the direct α-arylation of nitriles with aryl bromides
You, Jingsong,Verkade, John G.
, p. 8003 - 8007 (2007/10/03)
A new catalyst system for the synthesis of α-aryl-substituted nitriles is reported. The bicyclic triaminophosphine P(i-BuNCH 2CH2)3N (1b) serves as an efficient and versatile ligand for the palladium-catalyzed direct α-arylation of nitriles with aryl bromides. Using ligand 1b, ethyl cyanoacetate and primary as well as secondary nitriles are efficiently coupled with a wide variety of aryl bromides possessing electron-rich, electron-poor, electron-neutral, and sterically hindered groups.
A convenient and efficient palladium-catalyzed system for cross-coupling of aryl bromides with active methylene compounds
Gao, Chengwei,Tao, Xiaochun,Qian, Yanlong,Huang, Jiling
, p. 1716 - 1718 (2007/10/03)
A simply catalytic system containing palladium-phosphine complex, generated in situ from PdCl2/tert-phosphino ligand in pyridine, has been systematically studied in the cross-coupling of bromobenzene with malononitrile or ethyl cyanoacetate anion. The effect of molar ratio of phosphine ligand to PdCl2 on the activity of the coupling was also discussed. It is found that the catalytic system has highly catalytic activity to produce aryl malononitriles and cyanoacetates in considerable yields (67-90%) when the substituted aryl bromides were used as substrates.
Palladium-catalyzed arylation of malonates and cyanoesters using sterically hindered trialkyl- and ferrocenyldialkylphosphine ligands
Beare, Neil A.,Hartwig, John F.
, p. 541 - 555 (2007/10/03)
Palladium-catalyzed reactions of aryl bromides and chlorides with two common stabilized carbanions - enolates of dialkyl malonates and alkyl cyanoesters - are reported. An exploration of the scope of these reactions was conducted, and the processes were shown to occur in a general fashion. Using P(t-Bu)3 (1), the pentaphenylferrocenyl ligand (Ph5C5)Fe(C5H4)P(t-Bu) 2 (2), or the adamantyl ligand (1-Ad)P(t-Bu)2 (3), reactions of electron-poor and electron-rich, sterically hindered and unhindered aryl bromides and chlorides were shown to react with diethyl malonate, di-tertbutyl malonate, diethyl fluoromalonate, ethyl cyanoacetate, and ethyl phenylcyanoacetate. Although alkyl malonates and ethyl alkylcyanoacetates did not react with aryl halides using these catalysts, the same products were formed conveniently in one pot from diethylmalonate by cross-coupling of an aryl halide in the presence of excess base and subsequent alkylation.
A Convenient Synthesis of Some Arylated Phenylsulfonylacetonitriles and Ethyl Cyanoacetates Using Organo-iron Complexes
Abd-El-Aziz, Alaa S.,Denus, Christine R. de
, p. 293 - 298 (2007/10/02)
A general method for the synthesis of some arylated phenylsulfonylacetonitriles 6a-g, 10a, b and 16 and ethyl cyanoacetates 7a-d and 11a, b is described.Nucleophilic substitution of the cyclopentadienyliron complexes of chloroarenes 1a-g with phenylsulphonylacetonitrile 2 or ethyl cyanoacetate 3 in the presence of potassium carbonate in DMF, at room temperature under a nitrogen atmosphere gave cyclopentadienyliron complexes of arylated phenylsulphonylacetonitriles 4a-g, 8a, b and 15 and ethyl cyanoacetates 5a-d and 9a, b in very good yields (71-94percent).Photolysis of these complexes liberated the arenes (70-91percent).To demonstrate the versatility of this methodological approach, reactions of both carbon nucleophiles 2, 3 with dimethyl chlorobenzene complexes 1h, j gave the desired products 8a, 9a, 12 and 13 without significant steric effect.This synthesis is advantageous over all those previously reported and should be a practical route to a variety of alkanoic acid and heterocyclic precursors.
