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Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

ABSTRACT: The nickel-catalyzed synthesis of tetrasubstituted cyclobutenes from alkynes is reported. This transformation is uniquely promoted by the use of a primary aminophosphine, an unusual ligand in nickel catalysis. Mechanistic insights for this new transformation are provided, and postreaction modifications of the cyclobutene products to stereodefined cyclic and acyclic compounds are reported, including the synthesis of epi-truxillic acid.

SUBMITTER: Canellas S

PROVIDER: S-EPMC6470007 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature

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Nickel-Catalyzed Reductive [2+2] Cycloaddition of Alkynes.

Cañellas Santiago S Montgomery John J Pericàs Miquel À MÀ

Journal of the American Chemical Society 20181210 50

The nickel-catalyzed synthesis of tetrasubstituted cyclobutenes from alkynes is reported. This transformation is uniquely promoted by the use of a primary aminophosphine, an unusual ligand in nickel catalysis. Mechanistic insights for this new transformation are provided, and postreaction modifications of the cyclobutene products to stereodefined cyclic and acyclic compounds are reported, including the synthesis of epi-truxillic acid. ...[more]

PMID: 30517785

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