147795-55-9Relevant academic research and scientific papers
Efficient synthesis of a new, highly versatile chiral derivatizing agent, α-cyano-α-fluoro-p-tolylacetic acid (CFTA)
Takeuchi, Yoshio
, p. 365 - 366 (1998)
The new and versatile chiral derivatizing agent, α-cyano-α-fluoro-p-tolylacetic acid (CFTA), has been efficiently synthesized in optically pure form by Candida rugosa lipase-mediated kinetic resolution of racemic CFTA ethyl ester, the latter being readily
AlCl3 catalyzed coupling of: N-benzylic sulfonamides with 2-substituted cyanoacetates through carbon-nitrogen bond cleavage
Hu, Chen,Hong, Gang,Qian, Xiaofei,Kim, Kwang Rim,Zhu, Xiaoyan,Wang, Limin
supporting information, p. 4984 - 4991 (2017/07/10)
A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
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.
Metal-free photochemical aromatic perfluoroalkylation of α-cyano arylacetates
Nappi, Manuel,Bergonzini, Giulia,Melchiorre, Paolo
supporting information, p. 4921 - 4925 (2014/05/20)
We report here an operationally simple protocol for the direct aromatic perfluoroalkylation and trifluoromethylation of α-cyano arylacetates. This metal-free approach, which occurs at ambient temperature and under visible-light irradiation, is driven by t
Construction of 1,2,5-tricarbonyl compounds using methyl cyanoacetate as a glyoxylate anion synthon combined with copper(I) iodide-catalyzed aerobic oxidation
Kim, Se Hee,Kim, Ko Hoon,Kim, Jae Nyoung
supporting information; experimental part, p. 3335 - 3339 (2012/01/19)
A practical and efficient synthesis of various 1,2,5-tricarbonyl compounds is described. The synthesis has been carried out by a conjugate addition of methyl cyanoacetate to the β-position of α,β-unsaturated carbonyl compounds and a subsequent copper(I) iodide-catalyzed aerobic oxidation. In addition, various α-aryl- and α-alkyl-α-keto esters have been synthesized using a similar approach. Copyright
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 very reliable method for determination of absolute configuration of chiral secondary alcohols by 1H NMR spectroscopy
Takeuchi, Yoshio,Fujisawa, Hidehito,Noyori, Ryoji
, p. 4607 - 4610 (2007/10/03)
(Chemical equation presented) Surprisingly stable synperiplanar conformers of CFTA esters have led us to develop a new and very reliable method for assigning absolute configurations of even secondary alcohols having minimal structural differences, such as chiral benzhydrols and α-monodeuterated benzyl alcohols.
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.
