Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene

Scott E. Denmark, Mark E. Schnute

Research output: Contribution to journalArticlepeer-review

Abstract

Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd (OAc)2 (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 °C to afford exocyclic 2, 2-disubstituted-l-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.

Original languageEnglish (US)
Pages (from-to)1013-1019
Number of pages7
JournalJournal of Organic Chemistry
Volume60
Issue number4
DOIs
StatePublished - Feb 1 1995

ASJC Scopus subject areas

  • Organic Chemistry

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