Visible-light-promoted oxidation/condensation of benzyl alcohols with dialkylacetamides to cinnamides
Oxidative cross-coupling reactions of benzyl alcohols with N,N-dialkylacetamides were developed only employing oxygen as the terminal oxidant, efficiently providing a new, novel protocol for the construction of multifunctionalized cinnamides with the synergistic effects of KOH, organic photocatalyst eosin Y, and visible light irradiation at room temperature. A broad substrate scope and mild reaction conditions are the prominent features of this transformation.
Oxidative coupling of Michael acceptors with aryl nucleophiles produced through rhodium-catalyzed C-C bond activation
Utilizing rhodium catalysis, aryl nucleophiles generated via carbon-carbon single bond activation successfully undergo oxidative coupling with Michael acceptors. The reaction scope encompasses a broad range of nucleophiles generated from quinolinyl ketones as well as a series of electron deficient terminal alkenes, illustrating the broad potential of intersecting carbon-carbon bond activation with synthetically useful coupling methodologies. The demonstrated oxidative coupling produces a range of cinnamyl derivatives, several of which are challenging to prepare via conventional routes.
Gregerson, Caroline E.,Trentadue, Kathryn N.,Phipps, Erik J. T.,Kirsch, Janelle K.,Reed, Katherine M.,Dyke, Gabriella D.,Jansen, Jacob H.,Otteman, Christian B.,Stachowski, Jessica L.,Johnson, Jeffrey B.
p. 5944 - 5948
(2017/07/25)
Metal-Free Amidation of Acids with Formamides and T3P
A new, simple and metal-free method for the direct formation of dialkylamides from carboxylic acids employing N,N-dialkylformamides as amine source is described. The one-pot reaction is promoted by propylphosphonic anhydride (T3P) in the presence of 0.5 equivalents of HCl.
Bannwart, Linda,Abele, Stefan,Tortoioli, Simone
p. 2069 - 2078
(2016/07/06)
The Heck reaction of β-arylacrylamides: An approach to 4-aryl-2-quinolones
The Heck reaction of β-arylacrylamides with aryl iodides afforded the corresponding vinylic substitution products usually in high yields. The nature of β-substituents, aryl iodides and substituents at the nitrogen atom influences the stereochemical outcome. N,N-Dimethyl-β-arylacrylamides gave vinylic substitution products with higher stereoselectivity than the corresponding N-unsubstituted β-arylacrylamides. β-Arylacrylamides containing ortho-substituents led to the formation of only one stereoisomer. The procedure was used to prepare 4-aryl-2-quinolones from β-(obromophenyl) acrylamide through a sequential Heck reaction and copper-catalyzed cyclization process. Georg Thieme Verlag Stuttgart.
Sleep-Inducing N-Alkyl-5--5-hydroxy-2-pyrrolidinones and N-Alkyl-3-(trifluoromethyl)cinnamamides
A series of N-alkyl-3--5-hydroxy-2-pyrrolidinones and N-alkyl-3-(trifluoromethyl)-cinnamamides were prepared and screened in a series of tests designed to detect potential sleep inducers.The more active members of the series wer
Houlihan, William J.,Gogerty, John H.,Ryan, Eileen A.,Schmitt, Gemma
p. 28 - 31
(2007/10/02)
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