DNA-Compatible Suzuki-Miyaura Cross-Coupling Reaction of Aryl Iodides With (Hetero)Aryl Boronic Acids for DNA-Encoded Libraries

An efficient method for the C-C bond formation via water soluble Na2PdCl4/sSPhos mediated Suzuki-Miyaura cross-coupling reaction of DNA-conjugated aryl iodide with (het) aryl boronic acids has been developed. This reaction proceeds at 37 degrees C in water and acetonitrile (4:1) system. We also demonstrated that numerous aromatic and heteroaromatic boronic acids of different electronic natures, and harboring various functional groups, were highly compatible providing the desired coupling products in good to excellent yields. This DNA-compatible Suzuki-Miyaura cross-coupling reaction has strong potential to construct DNA-Encoded Libraries (DELs) in the context of drug discovery.

Automated summary

An efficient method for C-C bond formation was developed through water soluble Na2PdCl4/sSPhos mediated Suzuki-Miyaura cross-coupling reaction of DNA-conjugated aryl iodide with (het) aryl boronic acids. The reaction took place at 37 degrees C in a water and acetonitrile (4:1) system. Various aromatic and heteroaromatic boronic acids with different electronic properties and functional groups were compatible and resulted in high yields of desired coupling products. This DNA-compatible Suzuki-Miyaura cross-coupling reaction has strong potential for constructing DNA-Encoded Libraries (DELs) in the field of drug discovery.