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Nickel‐Catalyzed Dimerization and Alkylarylation of 1,3‐Dienes with Alkyl Fluorides and Aryl Grignard Reagents
Author(s) -
Iwasaki Takanori,
Min Xin,
Fukuoka Asuka,
Kuniyasu Hitoshi,
Kambe Nobuaki
Publication year - 2016
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.201601126
Subject(s) - alkyl , aryl , nickel , catalysis , reagent , chemistry , medicinal chemistry , polymer chemistry , organic chemistry
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.