Palladium-catalyzed oxidative arylhalogenation of alkenes: synthetic scope and mechanistic insights.

ABSTRACT: This article describes the development of a Pd-catalyzed reaction for the arylhalogenation (halogen = Cl or Br) of diverse alpha-olefins by oxidatively intercepting Mizoroki-Heck intermediates. These transformations afford synthetically useful 1,2- and 1,1-arylhalogenated products in good yields with good to excellent selectivities that can be modulated by changing the nature of the halogenating reagent and/or the reaction conditions. The selectivity of these reactions can be rationally tuned by (i) controlling the relative rates of oxidative functionalization versus beta-hydride elimination from equilibrating Pd(II)-alkyl species and (ii) stabilization of organometallic Pd(II) intermediates through the formation of pi-benzyl adducts. These arylhalogenations exhibit modest to excellent lev

SUBMITTER: Kalyani D 

PROVIDER: S-EPMC2895562 | biostudies-literature | 2010 Jun

REPOSITORIES: biostudies-literature