Solid‐Phase Microwave‐Assisted Ligand‐Free Suzuki‐Miyaura Cross‐Coupling of 5‐Iodouridine

Abstract

AbstractA soild‐supported 5‐iodouridine derivative underwent Suzuki‐Miyaura cross‐coupling reactions with various aryl/heteroarylboronic acids under microwave‐assisted ligand‐free conditions yielding 5‐aryl/heteroaryl uridine derivatives. Reactions were performed using Pd(dppf)Cl2 ⋅ CH2Cl2 as catalyst and K3PO4 as base in a tert‐BuOH/toluene/water solvent system. In our synthetic strategy uridine nucleosides were anchored onto 2‐chlorotrityl chloride resin through an acetal linkage blocking the 2′ – and 3′ –OH of the ribose moiety thus allowing an enormous opportunity for modifications on the nucleobase or on the 5′‐position. The described method offers an acid labile acetal linker strategy thus allowing potential application in Fmoc‐Solid‐Phase Peptide Synthesis or late stage modification of uridyl peptide nucleoside antibiotic analogues synthesis.