1609550-07-3Relevant 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.
Urea-catalyzed N-H insertion-arylation reactions of nitrodiazoesters
So, Sonia S.,Oottikkal, Shameema,Badji?, Jovica D.,Hadad, Christopher M.,Mattson, Anita E.
, p. 4832 - 4842 (2014/06/23)
The power of hydrogen-bond donor catalysis has been harnessed to elicit and control carbene-like reactivity from nitrodiazoesters. Specifically, select ureas have been identified as effective catalysts for N-H insertion and multicomponent coupling reactions of nitrodiazoesters, anilines, and aromatic nucleophiles, thereby preparing a variety of α-aryl glycines in high yield. Experimental and computational studies designed to probe the plausible reaction pathways suggest that difluoroboronate ureas are particularly well-suited to catalyze reactions of nitrodiazoesters with a range of anilines through a polar reaction pathway. Urea-facilitated loss of nitrite followed by addition of a nucleophile conceivably generates the observed aryl glycine products.
