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NHC/Nickel(II)-Catalyzed [3+2] Cross-Dimerization of Unactivated Olefins and Methylenecyclopropanes.
Angewandte Chemie International Edition ( IF 12.959 ) Pub Date : 2020-01-14 , DOI: 10.1002/anie.201914542
Jian-Qiang Huang,Chun-Yu Ho

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)]BArF catalyst (NHC=N-heterocyclic carbene). Results show that the C-C cleavage of 1 did not involve a Ni0 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/NiII -catalyzed rearrangement of 1 leads to the convergent synthesis of 3 in the presence of 2.
更新日期:2020-02-14

 

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