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Solid-phase rhodium carbenoid n-h insertion reactions: The synthesis of a diverse array of indoles

Academic Article
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Overview

authors

  • Lee, S. H.
  • Clapham, B.
  • Koch, G.
  • Zimmermann, J.
  • Janda, Kim

publication date

  • March 2003

journal

  • Journal of Combinatorial Chemistry  Journal

abstract

  • A solid-phase synthesis of an array of indoles is reported. The key step in our approach involves a N-H insertion reaction of N-alkylanilines into a highly reactive polymer-bound rhodium carbenoid intermediate to yield the corresponding alpha-arylamino-beta-ketoester. These insertion products were then treated under acid-catalyzed cyclodehydration conditions to yield a series of polymer-bound indole esters, which were subsequently cleaved from the resin under Lewis acid-promoted amidation conditions to yield the desired indoles in good yields and with excellent purities.

subject areas

  • Catalysis
  • Cyclization
  • Indicators and Reagents
  • Indoles
  • Resins, Synthetic
  • Rhodium
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Identity

International Standard Serial Number (ISSN)

  • 1520-4766

Digital Object Identifier (DOI)

  • 10.1021/cc020079z

PubMed ID

  • 12625710
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Additional Document Info

start page

  • 188

end page

  • 196

volume

  • 5

issue

  • 2

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