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NHC/Nickel(II)‐Catalyzed [3+2] Cross‐Dimerization of Unactivated Olefins and Methylenecyclopropanes
Author(s) -
Huang JianQiang,
Ho ChunYu
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201914542
Subject(s) - regioselectivity , carbene , chemistry , catalysis , methylenecyclopropane , alkene , nickel , reactivity (psychology) , umpolung , medicinal chemistry , cleavage (geology) , oxidative addition , stereochemistry , combinatorial chemistry , organic chemistry , materials science , medicine , alternative medicine , pathology , fracture (geology) , composite material , nucleophile
Cross‐dimerization of a methylenecyclopropane ( 1 ) and an unactivated alkene ( 2 ) with typical hydroalkenylation reactivity was observed for the first time by using a [NHC‐Ni(allyl)]BAr F catalyst (NHC=N‐heterocyclic carbene). Results show that the C−C cleavage of 1 did not involve a Ni 0 oxidative addition, which was crucial in former systems. Thus the method reported here emerges as a complementary method for attaining highly chemo‐ and regioselective synthesis of methylenecyclopentanes ( 3 ) with broad scope. An efficient NHC/Ni II ‐catalyzed rearrangement of 1 leads to the convergent synthesis of 3 in the presence of 2 .