Synlett 2013; 24(10): 1205-1210
DOI: 10.1055/s-0033-1338956
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© Georg Thieme Verlag Stuttgart · New York

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

Chenaimwoyo A. Gondo
Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland   Fax: +41(44)6322936   Email: bode@org.chem.ethz.ch
,
Jeffrey W. Bode
Laboratory of Organic Chemistry, Department of Chemistry and Applied Biosciences, ETH Zürich, Wolfgang-Pauli-Strasse 10, 8093 Zurich, Switzerland   Fax: +41(44)6322936   Email: bode@org.chem.ethz.ch
› Author Affiliations
Further Information

Publication History

Received: 12 April 2013

Accepted: 09 May 2013

Publication Date:
17 May 2013 (online)


Abstract

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.

Supporting Information

 
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