The overall aim of the study is to implement the Pd-catalyzed aminocarbonylation of aryl iodides to solid-phase chemistry, and in particular, solid phase peptide synthesis, by application of ex situ generated CO gas in a two-chamber system.1We have previously reported a simple and an expedient process to prepare 5-aryl-1-benzyl-1H-imidazole-4-carboxamides by the aminocarbonylation of 5-aryl-4-iodo-1H-imidazoles using ex situ generation of CO and with an amino acid amide as the nucleophile. The method was exploited to prepare imidazole-based constrained H-Phe-Phe-NH2 peptidomimetics.2 To enable a versatile introduction of various end capping groups to a peptide chain in the development of pseudopeptides and peptidomimetic, we foresee purification and reaction advantages by combining Fmoc-SPPS chemistry with Pd-catalyzed aminocarbonylations. Herein, results will be presented from an optimization process and substrate scope of aryl iodides and resin bound amino acids nucleophiles in an aminocarbonylation reaction using ex situ generation of CO gas.1. P. Hermange et al., JACS. 2011 , 133, 6061�60712. A. Skogh et al., J. Org. Chem. 2013  , 78, 12251�12256.

Aminocarbonylation of aryl iodides using solid-phase bound amino acid nucleophiles and ex situ generated CO gas

248th National Meeting (2014)

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