Palladium-catalyzed geometrically selective hydrogenation of (Z)-trifluoromethyl alkenyl triflate: an efficient approach to (Z) or (E)-3,3,3-trifluoropropenyl derivatives†,10.1039/C7OB00970D

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

Yilong Zhao,Yuhan Zhou,Chunxia Zhang,Huan Wang,Jinfeng Zhao,Kun Jin,Jihong Liu,Jianhui Liu,Jingping Qu

Organic & Biomolecular Chemistry Pub Date : 05/22/2017 00:00:00 , DOI:10.1039/C7OB00970D

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.