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

Chem Commun (Camb)

Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4 Raja S. C. Mullick Road, Jadavpur, Kolkata 700032, West Bengal, India.

Published: November 2024

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 C-labeled aryl carboxylic acids with satisfactory yields.

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http://dx.doi.org/10.1039/d4cc04758cDOI Listing

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