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Palladium‐Catalyzed Aerobic α,β‐Dehydrogenation of Carboxylic Acids

Palladium‐Catalyzed Aerobic α,β‐Dehydrogenation of Carboxylic Acids The aerobic dehydrogenation of saturated carboxylic acids to α,β‐unsaturated carboxylic acids proceeded by a simple Pd(OAc)2/pyridine catalyst system under 1 atm of O2. β‐Acyloxylated carboxylic acids were also produced from propionic acid and butyric acid by the conjugate addition of the substrates to the formed α,β‐unsaturated carboxylic acids. When propionic acid was used as a substrate, trans‐Pd(OCOEt)2(pyridine)2 was formed in situ as a precatalyst. The kinetic experiments indicated that Pd(OCOR)2(pyridine) is a catalytically active species and that β‐C(sp3)−H bond activation in the carboxylate ligand is the turnover‐limiting step. The DFT calculations agreed with the mechanism. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

Palladium‐Catalyzed Aerobic α,β‐Dehydrogenation of Carboxylic Acids

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References (1)

Publisher
Wiley
Copyright
© 2021 Wiley‐VCH GmbH
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.202100637
Publisher site
See Article on Publisher Site

Abstract

The aerobic dehydrogenation of saturated carboxylic acids to α,β‐unsaturated carboxylic acids proceeded by a simple Pd(OAc)2/pyridine catalyst system under 1 atm of O2. β‐Acyloxylated carboxylic acids were also produced from propionic acid and butyric acid by the conjugate addition of the substrates to the formed α,β‐unsaturated carboxylic acids. When propionic acid was used as a substrate, trans‐Pd(OCOEt)2(pyridine)2 was formed in situ as a precatalyst. The kinetic experiments indicated that Pd(OCOR)2(pyridine) is a catalytically active species and that β‐C(sp3)−H bond activation in the carboxylate ligand is the turnover‐limiting step. The DFT calculations agreed with the mechanism.

Journal

Asian Journal of Organic ChemistryWiley

Published: Dec 1, 2021

Keywords: carboxylic acids; dehydrogenation; oxygen; palladium; pyridine

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