Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins

Creators: Liu, Yiyang; Kim, Kelly E.; Herbert, Myles B.; Fedorov, Alexey; Grubbs, Robert H.; Stoltz, Brian M.

Abstract

A highly efficient palladium-catalyzed decarbonylative dehydration reaction of carboxylic acids is reported. This method transforms abundant and renewable even-numbered natural fatty acids into valuable and expensive odd-numbered alpha olefins. Additionally, the chemistry displays a high functional group tolerance. The process employs a low loading of palladium catalyst and proceeds under solvent-free and relatively mild conditions.

Additional Information

© 2014 Wiley-VCH Verlag GmbH & Co. Received: December 9, 2013; Published online: January 13, 2014. The authors wish to thank the Resnick Sustainability Institute at Caltech (graduate fellowship to Y.L.), BP (postdoctoral fellowship to A.F. under the XC2 program), NIH-NIGMS (R01GM080269, B.M.S.), NIH (NIH 5R01GM031332-27, R.H.G.), the Gordon and Betty Moore Foundation, the Caltech Center for Catalysis and Chemical Synthesis, and Caltech for financial support. Materia, Inc. is thanked for the generous donation of ruthenium catalysts. Dr. David Vander-Velde is acknowledged for NMR spectroscopy assistance. Dr. Mona Shahgholi and Naseem Torian are acknowledged for high-resolution mass spectrometry assistance. Dr. Scott Virgil is acknowledged for helpful discussions.

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Accepted Version - nihms-565526.pdf

Supplemental Material - adsc_201301109_sm_miscellaneous_information.pdf

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