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Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives

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Abstract

A Pd-catalyzed hydrogenation of (Z)-trifluoromethyl alkenyl triflate providing either (Z)- or (E)-3,3,3-trifluoropropenyl derivatives with excellent divergent geometric control in good yield is described. Catalyzed by Pd(OAc)2/PPh3, the reduction of (Z)-trifluoromethyl alkenyl triflates with HSiEt3 gave (E)-3,3,3-trifluoropropenyl derivatives, and while using HCOOH/Et3N as the reducing agent, the (Z)-isomers were obtained through an elimination/hydrogenation tandem pathway. Both transformations showed excellent geometrical selectivity.

Graphical abstract: Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives

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Publication details

The article was received on 20 Apr 2017, accepted on 22 May 2017 and first published on 22 May 2017


Article type: Paper
DOI: 10.1039/C7OB00970D
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives

    Y. Zhao, Y. Zhou, C. Zhang, H. Wang, J. Zhao, K. Jin, J. Liu, J. Liu and J. Qu, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB00970D

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