4714-17-4Relevant academic research and scientific papers
Palladium-catalyzed oxidative arylhalogenation of alkenes: Synthetic scope and mechanistic insights
Kalyani, Dipannita,Satterfield, Andrew D.,Sanford, Melanie S.
supporting information; experimental part, p. 8419 - 8427 (2010/08/04)
This article describes the development of a Pd-catalyzed reaction for the arylhalogenation (halogen = Cl or Br) of diverse α-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 β-hydride elimination from equilibrating PdII-alkyl species and (ii) stabilization of organometallic PdII intermediates through the formation of π-benzyl adducts. These arylhalogenations exhibit modest to excellent levels of stereoselectivity, and the key carbon-halogen bond-forming step proceeds with predominant retention of stereochemistry at carbon.
Oxidatively intercepting heck intermediates: Pd-catalyzed 1,2- and 1,1-arylhalogenation of alkenes
Kalyani, Dipannita,Sanford, Melanie S.
, p. 2150 - 2151 (2008/09/21)
This communication describes the development of two Pd-catalyzed reactions for the arylchlorination of diverse α-olefins by oxidatively intercepting Heck intermediates. Depending on the nature of the oxidant and the reaction conditions, these transformati
Catalytic Effect of Ferrous Chloride in Chloroarylation of Styrene
Obushak
, p. 443 - 445 (2007/10/03)
Styrene reacts with arenediazonium chlorides in the presence of FeCl2 as catalyst to give 1-chloro-1-phenyl-2-arylethanes along with minor amounts of 1,4-diaryl-2,3-diphenylbutanes. Ferrous chloride turned out to be a more active catalyst in the chloroarylation of styrene than copper chlorides.
