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General method for the preparation of active esters by palladium-catalyzed alkoxycarbonylation of aryl bromides. | LitMetric

General method for the preparation of active esters by palladium-catalyzed alkoxycarbonylation of aryl bromides.

J Org Chem

The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry and the Interdisciplinary Nanoscience Center, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus, Denmark.

Published: February 2015

AI Article Synopsis

Article Abstract

A useful method was developed for the synthesis of active esters by palladium-catalyzed alkoxycarbonylation of (hetero)aromatic bromides. The protocol was general for a range of oxygen nucleophiles including N-hydroxysuccinimide (NHS), pentafluorophenol (PFP), hexafluoroisopropyl alcohol (HFP), 4-nitrophenol, and N-hydroxyphthalimide. A high functional group tolerance was displayed, and several active esters were prepared with good to excellent isolated yields. The protocol was extended to access an important synthetic precursor to the HIV-protease inhibitor, saquinavir, by formation of an NHS ester followed by acyl substitution.

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Source
http://dx.doi.org/10.1021/jo5025464DOI Listing

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