278799-27-2Relevant articles and documents
Synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides
Liu, Jie,Fan, Chao,Yin, Hongyu,Qin, Chu,Zhang, Guoting,Zhang, Xu,Yi, Hong,Lei, Aiwen
, p. 2145 - 2147 (2014/02/14)
A silver catalysed synthesis of 6-acyl phenanthridines by oxidative radical decarboxylation-cyclization of α-oxocarboxylates and isocyanides was developed. This reaction provided a novel method to realize C1 insertion via a radical process and various functional groups were well-tolerated. The Royal Society of Chemistry.
Development of decarboxylative coupling processes for the synthesis of azomethines and ketones
Collet, Florence,Song, Bingrui,Rudolphi, Felix,Goossen, Lukas J.
experimental part, p. 6486 - 6501 (2011/12/05)
A bimetallic catalyst system has been developed that allows the synthesis of azomethines by a one-pot three-component decarboxylative coupling, starting from simple, nontoxic precursors, i.e. potassium α-oxo carboxylates, aryl halides and primary amines. In the presence of 15 mol-% copper/phenanthroline and 1 mol-% Pd/dppf, a wide range of valuable imines is conveniently accessible in high yields at 100 °C, an unprecedentedly low temperature for redox-neutral decarboxylative cross-coupling reactions. Hydrogenation of the azomethine products leads to secondary amines. Alternatively, they can be hydrolyzed in situ to aryl ketones. The resulting ketone synthesis via azomethine intermediates is also of interest as it gives higher yields at much lower temperatures than the direct decarboxylative coupling of α-oxo carboxylates with aryl halides. A convenient synthesis of azomethines by a one-pot three-component decarboxylative coupling, starting from potassium α-oxo carboxylates, aryl halides and primary amines is described. Combined with in situ hydrolysis, ketones are obtained. Thisamine-mediated ketone synthesis gives higher yields at lower temperatures than the direct coupling of α-oxo carboxylates. Copyright
Synthesis of ketones from α-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling
Goossen, Lukas J.,Rudolphi, Felix,Oppel, Christoph,Rodriguez, Nuria
, p. 3043 - 3045 (2008/12/23)
(Chemical Equation Presented) The power of two metals: A Pd/Cu catalyst system mediates the in situ formation of acyl nucleophiles by decarboxylation of readily accessible and stable salts of α-oxocarboxylic acids and their cross-coupling with aryl or heteroaryl bromides to give ketones. The reaction may be usedin the presence of many functional groups and provides good yields.
