title: Urea-catalyzed N-H insertion-arylation reactions of nitrodiazoesters.
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.
authors.affiliation: Department of Chemistry and Biochemistry, 100 West 18th Avenue, The Ohio State University , Columbus, Ohio 43210, United States.
authors.forename: Sonia S
authors.initials: SS
authors.lastname: So
authors.forename: Shameema
authors.initials: S
authors.lastname: Oottikkal
authors.forename: Jovica D
authors.initials: JD
authors.lastname: Badjić
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Hadad
authors.forename: Anita E
authors.initials: AE
authors.lastname: Mattson