Robust Suzuki–Miyaura Cross-Coupling on DNA-Linked
Substrates
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Abstract
The Suzuki–Miyaura cross-coupling
is one of the most widely
employed reactions in medicinal chemistry. To apply this reaction
to DNA-encoded library technology (ELT), an alternative approach in
the discovery of small molecule hits and leads, we explored the Suzuki–Miyaura
cross-coupling on DNA-linked aryl halides. Pd(PPh<sub>3</sub>)<sub>4</sub> was demonstrated to be an effective catalyst for cross-coupling
with on-DNA halide substrates under aqueous conditions. It efficiently
catalyzes the coupling of phenyl halides (iodide or bromide) and pyridinyl
bromides with various boronic acids/esters, including challenging
heterocyclic boronic acids/esters