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

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 modificati...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 140; no. 50; pp. 17349 - 17355
Main Authors Cañellas, Santiago, Montgomery, John, Pericàs, Miquel À
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.12.2018
Amer Chemical Soc
Subjects
Alkynes - chemistry
Catalysis
Chemistry
Chemistry, Multidisciplinary
Cycloaddition Reaction
Cyclobutanes - chemical synthesis
Ligands
Models, Chemical
Nickel - chemistry
Oxidation-Reduction
Phosphines - chemistry
Physical Sciences
Science & Technology
CYCLIZATIONS
HYDROGENATION
COUPLING REACTIONS
CYCLOBUTENES
RING
COMPLEXES
C-C
DIMERIZATION
DERIVATIVES
ALPHA-TRUXILLIC ACID
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Summary: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.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b09677