title: Trans-selective radical silylzincation of ynamides.
abstract: The silylzincation of terminal ynamides is achieved through a radical-chain process involving (Me3Si)3SiH and R2Zn. A potentially competing polar mechanism is excluded on the basis of diagnostic control experiments. The unique feature of this addition across the C≡C bond is its trans selectivity. One-pot electrophilic substitution of the C(sp2)-Zn bond by Cu(I)-mediated C-C bond formation and subsequent manipulation of the C(sp2)-Si bond provides a modular access to Z-α,β-disubstituted enamides.
authors.affiliation: Sorbonne Universités, UPMC Univ Paris 06, CNRS, UMR 8232, IPCM, CC 183, 4, place Jussieu, 75005 Paris (France).
authors.forename: Elise
authors.initials: E
authors.lastname: Romain
authors.forename: Carolin
authors.initials: C
authors.lastname: Fopp
authors.forename: Fabrice
authors.initials: F
authors.lastname: Chemla
authors.forename: Franck
authors.initials: F
authors.lastname: Ferreira
authors.forename: Olivier
authors.initials: O
authors.lastname: Jackowski
authors.forename: Martin
authors.initials: M
authors.lastname: Oestreich
authors.forename: Alejandro
authors.initials: A
authors.lastname: Perez-Luna
keywords: copper; radical reactions; silicon; silylmetalation; zinc