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In the presence of a nickel catalyst, 1,3-butadiene undergoes selective dimerization and alkylarylation with alkyl fluorides and aryl Grignard reagents to give 1,6-octadienes with alkyl and aryl groups at the 3- and 8-positions, respectively, by the consecutive formation of three carbon-carbon bonds. The formation of an anionic nickel complex plays an important role in forming C−C bonds with alkyl fluorides. [ABSTRACT FROM AUTHOR]

Ni-catalyzed dimerization of butadiene and subsequent alkylarylation reaction with arylmagnesium bromide and primary alkyl fluorides constitutes an efficient synthesis of 3-alkyl-8-aryl-1,6-octadienes. [ABSTRACT FROM AUTHOR]