Nickel Phosphite-Catalyzed Tetradehydro-Diels–Alder Reactions of (E)‑3-ene-1,8-diynes

A nickel-catalyzed tetradehydro-Diels–Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)–phosphite catalysts,...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 9; pp. 5391 - 5402
Main Authors Joyce, Liam M., Moggach, Stephen A., Hyland, Christopher J. T., Pyne, Stephen G., Stewart, Scott G.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.05.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,6-ENYNES
CYCLOADDITIONS
STEREOCHEMISTRY
COMPLEXES
C-C
CHEMISTRY
CYCLOISOMERIZATION
ALLENES
CYCLIZATION
ENYNES
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Summary:A nickel-catalyzed tetradehydro-Diels–Alder reaction of (E)-3-ene-1,8-diynes for the preparation of isoindolines, dihydroisobenzofurans, and tetrahydroisoquinolines has been developed. A series of air-stable nickel catalysts were used in this study, including the novel nickel(0)–phosphite catalysts, Ni­[P­(O-3,5-Me-Ph)3]4, Ni­[P­(O-1-naphthyl)3]4, and Ni­[P­(O-2-naphthyl)3]4. To help understand the type of intermediate in the initial cycloisomerization process, the trapping of nickellacycle intermediates with pinacolborane to yield vinyl boronates is also discussed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c03040