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[(NHC)Ni II H]‐Catalyzed Cross‐Hydroalkenylation of Cyclopropenes with Alkynes: Cyclopentadiene Synthesis by [(NHC)Ni II ]‐Assisted C−C Rearrangement
Author(s) -
Huang JianQiang,
Ho ChunYu
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201901255
Subject(s) - cyclopropene , alkyne , reactivity (psychology) , carbene , chemistry , catalysis , medicinal chemistry , cyclopentadiene , substrate (aquarium) , photochemistry , organic chemistry , medicine , oceanography , alternative medicine , pathology , geology
A cross‐hydroalkenylation/rearrangement cascade (HARC), using a cyclopropene and alkyne as substrate pairs, was achieved for the first time by using new [(NHC)Ni(allyl)]BAr F catalysts (NHC= N ‐heterocyclic carbenes). By controlling the (NHC)Ni II H relative insertion reactivity with cyclopropene and alkyne, a broad scope of cyclopentadienes was obtained with highly selectively. The structural features of the new (NHC)Ni II catalyst were important for the success of the reaction. The mild reaction conditions employed may serve as an entry for exploring (NHC)Ni II ‐assisted vinylcyclopropane rearrangement reactivity.