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Pt-Pd Nanoalloy for the Unprecedented Activation of Carbon-Fluorine Bond at Low Temperature

preprint
revised on 07.12.2019 and posted on 16.12.2019 by Raghu Nath Dhital, keigo nomura, Yoshinori Sato, Setsiri Haesuwannakij, Masahiro Ehara, Hidehiro Sakurai
Carbon-Fluorine (C-F) bonds are considered the most inert organic functionality and their selective transformation under mild conditions remains challenging. Herein, we report a highly active Pt-Pd nanoalloy as a robust catalyst for the transformation of C-F bonds into C-H bonds at low temperature, a reaction that often required harsh conditions. The alloying of Pt with Pd is crucial to activate C-F bond. The reaction profile kinetics revealed that the major source of hydrogen in the defluorinated product is the alcoholic proton of 2-propanol, and the rate-determining step is the reduction of the metal upon transfer of the beta-H from 2-propanol. DFT calculations elucidated that the key step is the selective oxidative addition of the O-H bond of 2-propanol to a Pd center prior to C-F bond activation at a Pt site, which crucially reduces the activation energy of the C-F bond. Therefore, both Pt and Pd work independently but synergistically to promote the overall reaction

Funding

JST(ACT-C) project (JPMJCR12YI)

History

Email Address of Submitting Author

hsakurai@chem.eng.osaka-u.ac.jp

Institution

Osaka University

Country

Japan

ORCID For Submitting Author

0000-0001-5783-4151

Declaration of Conflict of Interest

none

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in Bulletin of the Chemical Society of Japan

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