Premium
Nickel‐Catalyzed Regioselective Carbomagnesation of Methylenecyclopropanes through a Site‐Selective Carbon–Carbon Bond Cleavage
Author(s) -
Terao Jun,
Tomita Masahiro,
Singh Surya Prakash,
Kambe Nobuaki
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200904721
Subject(s) - regioselectivity , catalysis , reagent , nickel , chemistry , bond cleavage , aryl , cleavage (geology) , ring (chemistry) , medicinal chemistry , double bond , organic chemistry , polymer chemistry , combinatorial chemistry , materials science , alkyl , fracture (geology) , composite material
Unwringing the ring : Methylenecyclopropanes reacted with vinyl and aryl Grignard reagents in the presence of a nickel catalyst to afford vinyl‐ and arylmagnesation products, respectively, through a selective CC bond cleavage (see scheme). The reaction provides a new method for the preparation of substituted homoallyl and allyl Grignard reagents.