4.4 Article

Catalytic Redox Amidations of Aldehydes with a Polymer-Supported Peptide-N-Heterocyclic Carbene Multifunctional Catalyst

Journal

SYNLETT
Volume 24, Issue 10, Pages 1205-1210

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1338956

Keywords

N-heterocyclic carbenes; catalysis; immobilization; amides; solid-phase synthesis

Funding

  1. European Research Council [ERC] [306793 - CASAA]
  2. ETH Zurich

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We have prepared an oligomeric histidine-bound N-heterocyclic carbene precursor by coupling a carboxylic acid functionalized 1,2,4-triazolium salt to a peptide using solid-phase peptide synthesis. We have demonstrated that the resulting multifunctional resin-bound catalyst cooperatively facilitates redox amidation reactions of aldehydes and amines, a reaction not catalyzed by N-heterocyclic carbenes alone.

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