32191-53-0Relevant academic research and scientific papers
Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds
Bernardim, Barbara,Couch, Erica D.,Hardman-Baldwin, Andrea M.,Burtoloso, Antonio C. B.,Mattson, Anita E.
, p. 677 - 686 (2016/02/27)
Hydrogen-bond-donor catalysts enable a variety of formal insertion reactions of diazo compounds. The role of the catalyst in the reaction system may vary depending on several factors, including the nucleophilicity of the diazo compound and the acidity of the insertion partner. Ureas and phosphoric acid derivatives can offer complementary reactivity patterns when selected as catalysts for selected O-H and S-H insertion reactions of aryl- and diazo-substituted esters.
O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources
Mbuvi, Harun M.,Klobukowski, Erik R.,Roberts, Gina M.,Woo, L. Keith
experimental part, p. 284 - 292 (2010/12/19)
Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl, efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.
