19351-91-8Relevant academic research and scientific papers
Synthesis of functionalized pyrroles by reaction of 3,4-diacetylhexane-2,5- dione with primary amines in water
Yavari, Issa,Sabbaghan, Maryam
, p. 1791 - 1800 (2007)
3,4-Diacetylhexane-2,5-dione (tetra-acetylethane) undergoes a complex reaction with primary amines in boiling water to produce N-alkyl-3-acetyl-2,5- dimethylpyrroles, together with small quantities of N-alkyl-3,4-diacetyl-2,5- dimethylpyrroles and 2,5-dim
Manganese(III) acetate catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles
Zhang, Yaxing,Dong, Jianyu,Liu, Lixin,Liu, Long,Zhou, Yongbo,Yin, Shuang-Feng
supporting information, p. 2897 - 2901 (2017/04/11)
Mn-Catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles is disclosed, which enables the synthesis of a broad range of secondary amides in moderate to excellent yields under mild conditions. The interaction between Mn(iii) and DDQ facilitates the oxidation and makes it highly efficient and selective.
Base-promoted dehydrogenative coupling of benzene derivatives with amides or ethers
Ueno, Ryota,Shirakawa, Eiji
, p. 7469 - 7473 (2014/12/12)
Benzene derivatives are introduced into the dehydrogenative coupling via homolytic aromatic substitution (HAS) as arenes that couple with amides/ethers. NaOt-Bu is used as a critical promoter of HAS in combination with t-BuOOt-Bu as an oxidant.
Ritter reactions between alcohols and acetonitrile mediated by the conducting polymer poly-(3,4-ethylenedioxy thiophene) (Pedot)
D-Angelo, John G.,Cody, Jeremy A.,Larrabee, Christian,Ostrander, Danica J.,Rugg, Kyle W.,Mamangun, Donna
supporting information, p. 3224 - 3232 (2014/01/06)
Herein, we report new reactivity of the conducting polymer, poly-(3,4-ethylenedioxy thiophene) (PEDOT), where PEDOT mediates a Ritter reaction between alcohols and acetonitrile. The yields were variable and in most cases competitive with results obtained using sulfuric acid. Attempts at a stoichiometric reaction between benzonitrile and diphenylmethanol are also reported herein. Finally, described here are preliminary mechanistic studies that suggest PEDOT is behaving as an alcohol-selective or specific Lewis acid. Taylor & Francis Group, LLC.
Photo-ritter reaction of arylmethyl bromides in acetonitrile
Bi, Nai-Min,Ren, Ming-Guang,Song, Qin-Hua
experimental part, p. 2617 - 2623 (2010/10/03)
The photo-Ritter reaction of five arylmethyl bromides can occur in acetonitrile to give acetamides. The intermediates, carbocations, which are formed from subsequent electron transfer between the radical pairs generated from initial homolytic cleavage of the C-Br bond, are trapped by acetonitrile, and subsequent hydrolysis generates the corresponding acetamides. Taylor & Francis Group, LLC.
Alkylation of Rink's amide linker on polystyrene resin: A reductive amination approach to modified amine-linkers for the solid phase synthesis of N-substituted amide derivatives
Brown, Edward G.,Nuss, John M.
, p. 8457 - 8460 (2007/10/03)
Reductive amination of aldehydes and ketones using sodium cyanoborohydride and Rink's 4-(2',4'-dimethoxyphenyl-aminomethyl)-phenoxymethyl-linked polystyrene resin [Rink's amine linker on copoly-(styrene-1%-divinylbenzene)]1 2 affords high yields of linker-bound, N-alkyl amines with excellent chemical selectivity. Subsequent coupling with acid derivatives gave derivatized N-substituted amides in excellent yields after cleavage from the solid-support.
The Direct Synthesis of Secondary Amides from Aldehydes; A Novel General Redox Procedure Mediated by Iodotrichlorosilane (ITCS)
Elmorsy, Saad S.,Badawy, Doria S.,Nour, Mohamed A.,Kandeel, Ezzat M.
, p. 417 - 421 (2007/10/02)
A unique, general redox process for the preparation of secondary amides by the interaction, of aldehydes with nitriles in the presence of two equivalents of iodotrichlorosilane (ITCS) is described and possible pathways are discussed. - Keywords: Iodotrichlorosilane, Aldehydes, Nitriles, sec-Amides
Photolysis of (Arylmethyl)triphenylphosphonium Salts. Substituent, Counterion, and Solvent Effects on Reaction Products
Imrie, C.,Modro, T. A.,Rohwer, E. R.,Wagener, C. C. P.
, p. 5643 - 5649 (2007/10/02)
Quaternary (arylmethyl)phosphonium salts of the general formula ArCH2-PR3(+)Y(-) (Ar = substituted phenyl or 1-naphthyl; R = phenyl, ferrocenyl, or butyl; Y(-) = BF4(-) or halide) have been photolyzed in acetonitrile or in methanol.Photolysis involved the cleavage of the P-CH2 bond and the products derived from both, the arylmethyl radical and the carbocation, were formed.The proportion of the radical- and carbocation-derived products was determined as a function of substituents in group Ar, of groups R, counterions Y(-), and the solvent.For the nonoxidizable counterion (BF4(-), the proposed mechanism of the reaction involves initial homolysis, followed by the escape of the radical products from a solvent cage, or by the electron transfer from carbon to phosphorus, yielding the corresponding arylmethyl carbocation.The latter can either react with the solvent to form the observed carbocation-derived product or can undergo recombination with the tertiary phosphine formed to yield the starting phosphonium ion.Some indication of the "inverted substituent effect" resulting from the inhibition of single electron transfer from an easily oxidized radical was obtained.For the oxidizable counterions (halides), an additional pathway is suggested, that involves electron transfer from the anion, yielding the arylmethyl radical and the phosphine, thus decreasing the ionic/radical products ratio.
SYNTHESIS OF N-BENZYL- AND N-HETEROARYLMETHYL-ACYLAMIDES BY REDUCTIVE N-ACYLATION OF ALDOXIMES WITH AMMONIUM FORMATE
Balicki, Roman,Kaczmarek, Lukasz
, p. 525 - 526 (2007/10/02)
Various (hetero)aryl aldoximes have been efficiently transformed to the corresponding acylamides via reductive N-acylation, catalyzed by 10percent palladium on carbon in the presence of ammonium formate as the hydrogen source in an alkanoic acid.
A NOVEL ROUTE FOR THE DIRECT SYNTHESIS OF SECONDARY AMIDES FROM ALDEHYDES
Elmorsy, Saad S.,Nour, Mohamed A.,Kandeel, Ezzat M.,Pelter, Andrew
, p. 1825 - 1826 (2007/10/02)
We describe a unique, general redox process for the preparation of secondary amides by the interaction of aldehydes and nitriles in the presence of two equivalents of iodotrichlorosilane (ITCS).
