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A phosphine-free palladium catalyst for aqueous Suzuki-Miyaura cross-coupling is presented. The catalyst is active enough to mediate hindered, ortho-substituted biaryl couplings but mild enough for use on peptides and proteins. The Suzuki-Miyaura couplings on protein substrates are the first to proceed in useful conversions. Notably, hydrophobic aryl and vinyl groups can be transferred to the protein surface without the aid of organic solvent since the aryl- and vinylboronic acids used in the coupling are water-soluble as borate salts. The convenience and activity of this catalyst prompts use in both general synthesis and bioconjugation.

Original publication

DOI

10.1021/ja907150m

Type

Journal article

Journal

J Am Chem Soc

Publication Date

18/11/2009

Volume

131

Pages

16346 - 16347

Keywords

Bacillus, Boronic Acids, Catalysis, Microwaves, Molecular Structure, Palladium, Stereoisomerism, Structure-Activity Relationship, Subtilisin, Water