137936-56-2Relevant academic research and scientific papers
Palladium-Catalyzed Regioselective Allylation of 6,6-Dimethylfulvene: A New Fulvene Synthesis
Nystroem, Jan-Erik,Vagberg, Jan O.,Soederberg, Bjoern C.
, p. 5247 - 5250 (1991)
6,6-Dimethylfulvene was regioselectively functionalized at the 7-position by reacting the fulvene anion 1 with allylic chlorides or allylic acetates in the presence of palladium(0)-phosphine catalyst. Key words: Palladium-catalyzed; exocyclic allylation; regio- and chemoselective; fulvene
Regioselective Palladium-Catalyzed Allylation of Fulvenes
Soederberg, Bjoern C.,Austin, Lucinda R.,Davis, Carol A.,Nystroem, Jan-Erik,Vagberg, Jan O.
, p. 61 - 76 (2007/10/02)
Fulvene-anions (vinyl cyclopentadienyl anions) are exclusively allylated in the exocyclic position by allylic chlorides, allylic acetates, and allylic carbonates in the presence of catalytic amounts of bis(dibenzylideneacetone)palladium(0) and triphenyl phosphine in good to excellent yield.A high degree of regioselectivity is observed with regard to the allylic substrate, and the most hindered position was predominately substituted.Inversion of stereochimistry of the allylic carbon by migration of the anion from the metal, of an intermediate η3-allylpalladium complex, to carbon is observed.
