4.8 Article

Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes

Journal

ORGANIC LETTERS
Volume 18, Issue 24, Pages 6428-6431

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03326

Keywords

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Funding

  1. West Virginia University
  2. NSF [CHE-1559654]
  3. NSF Major Research Instrumentation (MRI) Program [CHE-1228336, CHE-1336071, CHE-1427136]
  4. Direct For Mathematical & Physical Scien [1427136, 1559654] Funding Source: National Science Foundation
  5. Division Of Chemistry [1427136, 1559654] Funding Source: National Science Foundation

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Regioselective copper-catalyzed boracarboxylation of vinyl arenes with bis(pinacolato)diboron and carbon dioxide has been achieved. New boron-functionalized alpha-aryl carboxylic acids, including nonsteroidal anti-inflammatory drugs (NSAIDs), are obtained in moderate to excellent yields. The synthetic utility of the transformation was shown through subsequent derivatization of the carbon-boron bond yielding formal hydroxy- and fluorocarboxylation products as well as anionic difluoroboralactones.

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