1126-56-3Relevant articles and documents
Catalytic hydrogenation of amides to amines under mild conditions
Stein, Mario,Breit, Bernhard
supporting information, p. 2231 - 2234 (2013/03/28)
Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright
An efficient catalytic method for the Beckmann rearrangement of ketoximes to amides and aldoximes to nitriles mediated by propylphosphonic anhydride (T3P)
Augustine, John Kallikat,Kumar, Rajesha,Bombrun, Agnes,Mandal, Ashis Baran
scheme or table, p. 1074 - 1077 (2011/03/22)
An efficient method for the Beckmann rearrangement of ketoximes to amides mediated by a catalytic amount (15 mol %) of propylphosphonic anhydride (T3P) is described. Aldoximes underwent second order Beckmann rearrangement to provide the corresponding nitriles in excellent yields on reacting with T3P (15 mol %) at room temperature. The main advantages of this environmentally friendly protocol include procedural simplicity, and particularly ease of isolation of the products.
Safe and efficient ritter reactions in flow
Brandt, Johan C.,Elmore, Simon C.,Robinson, Richard I.,Wirth, Thomas
experimental part, p. 3099 - 3103 (2011/02/25)
Efficient mixing, temperature control and small environmental exposures allow reactions carried out in microfluidic de-vices to perform superior to their batch-type counterparts in conventional flasks. The Ritter reaction has been optimised for flow conditions leading to short reaction times and higher yields and also is more feasible with regards to safety, productivity and tolerance towards substrate functionalities.
A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions
Kang, Dong Ho,Joo, Tae Young,Lee, Eun Hwa,Chaysripongkul, Skaydaw,Chavasiri, Warinthorn,Jang, Doo Ok
, p. 5693 - 5696 (2007/10/03)
Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.
Synthesis of dendritic oligo(aryl sulfone)s as supports for synthesis
Taylor, Paul C.,Wall, Michael D.,Woodward, Peter R.
, p. 12314 - 12322 (2007/10/03)
A short, divergent route to G1 oligo(aryl sulfone)s and a G 2 oligo(aryl sulfone) dendrimer using nucleophilic aromatic substitution reactions is described. A range of tetrasubstituted pentasulfones are proposed for applications as homogeneous supports for synthesis. Key to achieving selectivity in the syntheses is the activation of leaving groups by sulfide to sulfone oxidation. Preparation of the G2 oligo(aryl sulfone) is low-yielding due to competition from SET processes that are interesting from a mechanistic point of view. The utility of the supports is exemplified with a four step synthesis of a dipeptide and by 'react and release' synthesis of amides.
Dephosphonylation of β-carbonyl phosphonates
Lee, Shi Yong,Lee, Chi-Wan,Oh, Dong Young
, p. 7017 - 7022 (2007/10/03)
A new methodology has been developed for the P-C bond cleavage of β- carbonyl phosphonates. The α,α-disubstituted β-keto phosphonates and the α-carbamoyl phosphonates have been shown to undergo dephosphonylation by reaction of their lithium enolate with LiAlH4, followed by quenching with aqueous H2SO4, affording regioselectively α,α-disubstituted ketone and α-substituted and α,α-disubstituted secondary amides.
Asymmetric Catalysis by Vitamin B12: The Isomerization of Achiral Aziridines to Optically Active Allylic Amines
Zhang, Zhong da,Scheffold, Rolf
, p. 2602 - 2615 (2007/10/02)
Achiral N-acylaziridines are isomerized to optically active N-acyl-allylamines in ee's of up to 95percent by catalytic amounts of cob(I)alamin in MeOH.
The Amidation of Carboxylic Acid with Amine over Hydrous Zirconium(IV) Oxide
Takahashi, Kyoko,Shibagaki, Makoto,Kuno, Hideyuki,Kawakami, Hiroshi,Matsushita, Hajime
, p. 1333 - 1334 (2007/10/02)
The reaction of a carboxylic acid or an ester with an amine to give the corresponding amide was carried out efficiently over hydrous zirconium(IV) oxide, whether in the vapor phase or in the liquid phase.
NEW SYNTHETIC 'TRICKS'. ADVANTAGES OF USING TRIETHYLPHOSPHINE IN SOME PHOSPHORUS-BASED REACTIONS
Urpi, Felix,Vilarrasa, Jaume
, p. 4623 - 4624 (2007/10/02)
It is shown that Et3P can advantageously replace Ph3P, Bu3P, and other P(III) reagents in phosphazene reactions (amide and phthalimide formation) and disulphide-cleavage-based reactions (reduction of disulphides, thioester formation, and oxime hydrolysis).
NEW SYNTHETIC "TRICKS". TRIPHENYLPHOSPHINE-MEDIATED AMIDE FORMATION FROM CARBOXYLIC ACIDS AND AZIDES
Garcia, Jordi,Urpi, Felix,Villarasa, Jaume
, p. 4841 - 4844 (2007/10/02)
Equimolar amounts of carboxylic acids, aryl or alkyl azides, and Ph3P in refluxing benzene (hexane, toluene) afford amides in good yields.Insolubility of zwitterions Ph3P(+)-NH(CH2)nCOO(-), arising from ω-azido acids and Ph3P, limits the utilization of the method for lactame formation.
