Urea-catalyzed N-H insertion-arylation reactions of nitrodiazoesters.
Sonia S So, Shameema Oottikkal, Jovica D Badjić, Christopher M Hadad, Anita E Mattson
Index: J. Org. Chem. 79(11) , 4832-42, (2014)
Full Text: HTML
Abstract
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.
Related Compounds
Related Articles:
Arylation of diazoesters by a transient N-H insertion organocascade.
2013-10-18
[Angew. Chem. Int. Ed. Engl. 52(43) , 11317-20, (2013)]
Urea-catalyzed construction of oxazinanes.
2013-09-21
[Org. Biomol. Chem. 11(35) , 5793-7, (2013)]
Internal Lewis acid assisted ureas: tunable hydrogen bond donor catalysts.
2013-05-14
[Chem. Commun. (Camb.) 49 , 4289-4291, (2013)]
Boronate urea activation of nitrocyclopropane carboxylates.
2012-01-20
[Org. Lett. 14(2) , 444-7, (2012)]
Internal Lewis acid assisted hydrogen bond donor catalysis.
2011-02-18
[Org. Lett. 13(4) , 716-9, (2011)]