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Ni‐Catalyzed Cascade Cyclization–Kumada Alkyl–Alkyl Cross‐Coupling
Author(s) -
GuisánCeinos Manuel,
SolerYanes Rita,
ColladoSanz Daniel,
Phapale Vilas B.,
Buñuel Elena,
Cárdenas Diego J.
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300882
Subject(s) - alkyl , catalysis , cascade , chemistry , reagent , alkene , beta hydride elimination , medicinal chemistry , catalytic cycle , ethylenediamine , coupling (piping) , organic chemistry , materials science , chromatography , metallurgy
Suggesting novel disconnections : A powerful Ni‐catalyzed cascade reaction involving cyclization followed by cross‐coupling allows the formation of up to three alkyl–alkyl bonds in a single operation by using alkene‐containing alkyl iodides and Grignard reagents (see scheme; acac=acetylacetonate; TMEDA= N , N ′, N ′‐tetramethyl ethylenediamine). Mechanistic experimental and computational studies suggest a Ni I –Ni II –Ni III catalytic cycle and the intermediacy of radicals.