26926-35-2Relevant articles and documents
Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement
Kumar, Arun,Kumar, Naveen,Sharma, Ritika,Bhargava, Gaurav,Mahajan, Dinesh
, p. 11323 - 11334 (2019/09/10)
Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.
Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O2
Gonzalez-De-Castro, Angela,Xiao, Jianliang
supporting information, p. 8206 - 8218 (2015/07/15)
A mild and operationally simple iron-catalyzed protocol for the selective aerobic oxidation of aromatic olefins to carbonyl compounds is described. Catalyzed by a Fe(III) species bearing a pyridine bisimidazoline ligand at 1 atm of O2, α- and β-substituted styrenes were cleaved to afford benzaldehydes and aromatic ketones generally in high yields with excellent chemoselectivity and very good functional group tolerance, including those containing radical-sensitive groups. With α-halo-substituted styrenes, the oxidation took place with concomitant halide migration to afford α-halo acetophenones. Various observations have been made, pointing to a mechanism in which both molecular oxygen and the olefinic substrate coordinate to the iron center, leading to the formation of a dioxetane intermediate, which collapses to give the carbonyl product. (Chemical Equation).
Phase-Transfer Catalyzed Synthesis of Amides and Esters of Carboxylic Acids
Jaszay, Zsuzsa M.,Petnehazy, Imre,Toeke, Laszlo
, p. 745 - 747 (2007/10/02)
A convenient one-pot procedure is reported for the preparation of carboxamides and carboxylic acid esters from carboxylic acids and amines or alcohols, respectively.The carboxylic acids are activated by sulfonyl chlorides under solid-liquid phase-transfer conditions using solid potassium carbonate as base and a lipophilic quaternary ammonium salt as catalyst.
