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

SS So, AE Mattson - Journal of the American Chemical Society, 2012 - ACS Publications
SS So, AE Mattson
Journal of the American Chemical Society, 2012ACS Publications
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.
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.
ACS Publications
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