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Nickel‐Catalyzed Regioselective Three Component Coupling Reaction of Alkyl Halides, Butadienes, and Ar‐M (M=MgX, ZnX)
Author(s) -
Terao Jun,
Nii Shinsuke,
Chowdhury Firoz A.,
Nakamura Akifumi,
Kambe Nobuaki
Publication year - 2004
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200404041
Subject(s) - chemistry , alkyl , halide , regioselectivity , reagent , catalysis , aryl , nickel , coupling reaction , alkylation , medicinal chemistry , organic chemistry
A new method for the regioselective three component cross‐coupling reaction of alkyl halides, 1,3‐butadienes, and aryl‐Grignard reagents has been developed by the use of a nickel catalyst. This reaction proceeds efficiently at 25 °C using (dppf)NiCl 2 as a catalyst. Alkyl chlorides, bromides, and iodides can be used as suitable alkylating reagents. The reaction also proceeds when arylzinc halides are used instead of Grignard reagents. Competitive reactions of a mixture of primary, secondary, and tertiary alkyl bromides showed that the reactivities of the halides increase in the order primary