Palladium-Catalyzed 1,2- and 1,1-Aryl-halogenation of Alkenes

Significance

Pd-alkyl species resulting from C-H activation, olefin aminopalladation and enyne cyclization were shown to be oxidatively interceptable by hypervalent I(III) reagents. In this article, it is demonstrated that a β-hydride elimination in Heck coupling reactions with aryltin reagents can be successfully out-competed by the use of the chlorinating oxidants PhICl₂ and CuCl₂. Thus, both 1,1- and 1,2-arylhalogenated alkanes could be obtained.