RESUMEN
We report a palladium-catalyzed, three-component carbosilylation reaction of internal symmetrical alkynes, silicon electrophiles, and primary alkyl zinc iodides. Depending on the choice of ligand, stereoselective synthesis of either cis- or trans-tetrasubstituted vinyl silanes is possible. We also demonstrate conditions for the Hiyama cross-coupling of these products to prepare geometrically defined tetrasubstituted alkenes.
Asunto(s)
Silanos/síntesis química , Compuestos de Vinilo/síntesis química , Alquinos/química , Catálisis , Yoduros/química , Ligandos , Estructura Molecular , Paladio/química , Silanos/química , Silicio/química , Estereoisomerismo , Compuestos de Vinilo/química , Compuestos de Zinc/químicaRESUMEN
A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29-95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C-O, C-C, and C-N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N-O bond.