Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 3, Pages 1920-1928Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo5025464
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Funding
- Danish National Research Foundation [DNRF59]
- Villum Foundation
- Danish Council for Independent Research: Technology and Production Sciences
- Lundbeck Foundation
- Carlsberg Foundation
- Aarhus University
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior (CAPES) [BEX 6280/13-7]
- FAPEMIG
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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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