Urea activation of α-nitrodiazoesters: an organocatalytic approach to N-H insertion reactions

Journal of the American Chemical Society
Sonia S So, Anita E Mattson

Abstract

The combination of a urea catalyst and an α-nitro-α-diazo ester gives rise to a reactive species able to undergo insertion into the N-H bonds of anilines. This new strategy to achieve N-H insertion reactivity is in contrast to typical metal-catalyzed conditions for the generation of carbenoids from α-diazocarbonyl compounds. This report includes the extension of the insertion reaction to a three-component coupling for the construction of α-amino-α-aryl esters in high yield.

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Citations

Sep 28, 2013·Organic Letters·David M NickersonAnita E Mattson
Mar 10, 2016·The Journal of Organic Chemistry·Xuesong LuoXueliang Huang
Aug 19, 2015·Chemical Reviews·Alan FordM Anthony McKervey
Jul 12, 2016·The Journal of Organic Chemistry·Eddy I JiménezMarcos Hernández-Rodríguez
Sep 7, 2016·The Journal of Organic Chemistry·Anna ChentsovaKerry Gilmore
Sep 13, 2016·The Journal of Organic Chemistry·Saghar NourianJohn P Toscano
Oct 18, 2014·Journal of the American Chemical Society·Ryan R WalvoordMarisa C Kozlowski
Oct 21, 2014·ChemSusChem·Andrea M Hardman-Baldwin, Anita E Mattson
Jun 4, 2014·Chemistry : a European Journal·Erica D CouchAnita E Mattson
Aug 3, 2013·Organic & Biomolecular Chemistry·Andrea M HardmanAnita E Mattson
Sep 17, 2013·Angewandte Chemie·Tyler J AuvilAnita E Mattson
Feb 14, 2014·Chemical Communications : Chem Comm·Takuya HashimotoKeiji Maruoka
Nov 5, 2014·Angewandte Chemie·Veronica V Angeles-DunhamAnita E Mattson
Jun 26, 2018·Chemical Science·Igor D Jurberg, Huw M L Davies
Feb 4, 2014·Chemical Science·Z Jane WangFrances H Arnold
Oct 14, 2014·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Madhappan Santha MoorthyChang-Sik Ha
Dec 1, 2012·Chemical Communications : Chem Comm·David M NickersonAnita E Mattson
May 7, 2014·The Journal of Organic Chemistry·Sonia S SoAnita E Mattson

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