Postsynthetic Modification of Peptoids via the Suzuki-Miyaura Cross-Coupling Reaction

Abstract

We developed a new method for modifying the side chains of peptoids on a solid phase resin, employing the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. Optimized conditions using Pd(PPh3)(4) and K2CO3 in the presence of Buchwald's SPhos ligand provided a high conversion in the coupling reaction. The usefulness of this method was demonstrated by synthesis of a two pyrene-conjugated peptoid helix, which exhibited an interesting excimer formation. (C) 2015 Wiley Periodicals, Inc.