Nickel‐Catalyzed Kumada Coupling of Benzyl Chlorides and Vinylogous Derivatives | Zendy

SolerYanes Rita | Zendy; GuisánCeinos Manuel | Zendy; Buñuel Elena | Zendy; Cárdenas Diego J. | Zendy

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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.

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