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Published January 13, 2014 | Version Supplemental Material + Accepted Version
Journal Article Open

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

Creators

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.

Attached Files

Accepted Version - nihms-565526.pdf

Supplemental Material - adsc_201301109_sm_miscellaneous_information.pdf

Files

adsc_201301109_sm_miscellaneous_information.pdf

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Additional details

Identifiers

PMCID
PMC3998208
Eprint ID
43475
Resolver ID
CaltechAUTHORS:20140122-135551444

Funding

Resnick Sustainability Institute
BP XC2 Program
NIH
R01GM080269
NIH
5R01GM031332-27
Gordon and Betty Moore Foundation
Caltech Center for Catalysis and Chemical Synthesis

Dates

Created
2014-01-22
Created from EPrint's datestamp field
Updated
2020-07-07
Created from EPrint's last_modified field

Caltech Custom Metadata

Caltech groups
Resnick Sustainability Institute