Peptide modification via a mild carbonylative Suzuki-Miyaura reaction gives late-stage access to diaryl-ketones

Abstract

Benzophenones and other diaryl ketones are common handles for photo-crosslinking and photo-affinity labelling. Here, we introduce the use of an operationally simple carbonylative Suzuki-Miyaura cross-coupling for the late-stage introduction of these handles into unprotected peptides. By using molybdenum hexacarbonyl, Mo(CO)₆, as a carbon monoxide surrogate, these reactions take place under mild aqueous conditions, under an open (air) atmosphere, requiring no specialist equipment or techniques.