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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

Release Time:2019-03-12  Hits:

Indexed by: Journal Article

Date of Publication: 2017-07-21

Journal: ORGANIC & BIOMOLECULAR CHEMISTRY

Included Journals: PubMed、EI、SCIE

Volume: 15

Issue: 27

Page Number: 5693-5700

ISSN: 1477-0520

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.

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