A chemoselective hydroxycarbonylation and 13C-labeling of aryl diazonium salts using formic acid as the C-1 source

Abstract

We report a one-pot synthesis of aryl carboxylic acids utilizing HCOOH as a CO surrogate with low Pd-catalyst loading. This operationally simple and scalable method does not require use of a high-pressure reactor, two-chamber reaction vessel, phosphine ligand, or base and proceeds in a relatively short amount of time at ambient temperature. Notably, halides, including iodo and bromo groups, and nitro groups remain intact under these mild reaction conditions. This methodology has been successfully applied to synthesizing ¹³C-labeled aryl carboxylic acids with satisfactory yields.