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Nickel‐Catalyzed Kumada Coupling of Benzyl Chlorides and Vinylogous Derivatives
Author(s) -
SolerYanes Rita,
GuisánCeinos Manuel,
Buñuel Elena,
Cárdenas Diego J.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403007
Subject(s) - chemistry , catalysis , reagent , electrophile , ethylenediamine , ether , nickel , medicinal chemistry , organic chemistry , coupling reaction , polymer chemistry
Conditions for the fast Ni‐catalyzed Kumada‐type cross‐coupling of functionalized benzyl and allyl chlorides with alkylmagnesium reagents were discovered. The use of Ni(acac) 2 –TMEDA (acac = acetylacetonate, TMEDA = N , N , N′ , N′ ‐tetramethyl‐1,2‐ethylenediamine) allows the presence of reactive functional groups on the electrophile. On the other hand, the use of diallyl ether was shown to provide fast coupling at low temperature with a low catalyst loading. The reaction seems to follow a radical pathway.