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

Liam M. Joyce, Stephen A. Moggach, Christopher J.T. Hyland, Stephen G. Pyne, Scott G. Stewart

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5391-5402
Number of pages12
JournalJournal of Organic Chemistry
Volume88
Issue number9
DOIs
Publication statusPublished - 5 May 2023

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