title: Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins.
abstract: The palladium-catalyzed cross-coupling reactions of (E)- or (Z)-1-fluorovinylstannanes with aryl iodides and vinyl iodides provide good yields of stereoisomerically pure substituted fluoroolefins with retention of the double bond geometry. The reaction takes place with copper(I) iodide present as a cocatalyst at ambient temperature or in refluxing tetrahydrofuran and is tolerant of a variety of functional groups. Highly functionalized and stereoisomerically pure monofluorovinyl ketones also were obtained under mild conditions by the coupling of 1-fluorovinylstannanes with acid chlorides. (1)H-{(19)F} NOE NMR experiments unequivocally established the stereochemistry of the coupling products E-14 and Z-14.
authors.affiliation: Department of Medicinal Chemistry, Neurocrine Biosciences, Inc., 10555 Science Center Drive, San Diego, California 92121.
authors.forename: Chen
authors.initials: C
authors.lastname: Chen
authors.forename: Keith
authors.initials: K
authors.lastname: Wilcoxen
authors.forename: Yun-Fei
authors.initials: YF
authors.lastname: Zhu
authors.forename: Kyung-il
authors.lastname: Kim Ki
authors.forename: James R.
authors.initials: JR
authors.lastname: McCarthy