60498-68-2Relevant articles and documents
Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
da Silva, Amanda F.,Afonso, Marco A. S.,Cormanich, Rodrigo A.,Jurberg, Igor D.
, p. 5648 - 5653 (2020/04/22)
A visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates. Alternatively, photochemical reactions show a broad scope, can be performed under air and tolerate a wide variety of functional groups. Reaction-evolution monitoring, DFT calculations and control experiments have been used to evaluate the main aspects of this intricate mechanistic scenario. Biologically active molecules Adiphenine, Benactyzine and Aprophen have been prepared as examples of synthetic applications.
Concave pyridines for selective acylations of polyols
Luening, Ulrich,Petersen, Soenke,Schyja, Wolfgang,Hacker, Wolfgang,Marquardt, Torsten,Wagner, Kerstin,Bolte, Michael
, p. 1077 - 1084 (2007/10/03)
Selectivity enhancements in the base-catalyzed acylation of polyols (1,2- or 1,3-alkanediol, partially protected glucoside) have been found with (bi)macrocyclic pyridines 2 and 9 as catalysts. The different selectivities obtained for concave pyridines of varying ring sizes (1 vs. 2) are probably caused by their different geometries as a number of X-ray analyses (1a, 1b, 2a, 2b, 2e, 9) indicate. The methyl glucoside 7 can selectively be acylated in 2-position.
A NEW GENERAL METHOD FOR THE PREPARATION OF CARBOXYLIC ACID ESTERS
Froeyen, Paul
, p. 145 - 152 (2007/10/02)
Esters can be generated directly in good yields under mild conditions from the corresponding carboxylic acid and alcohol in the presence of equivalent amounts of pyridine, triphenylphosphine and N-halosuccinimide.Key words: Carboxylic acids, esterification, triphenylphosphine, N-halo succinimides.