Synthesis of Bicyclic Nitrogen Compounds via Tandem Intramolecular Heck Cyclization and Subsequent Trapping of Intermediate π-Allylpalladium Complexes

G. Davis Harris, R. Jason Herr, Steven M. Weinreb

Research output: Contribution to journalArticle

53 Citations (Scopus)

Abstract

Intramolecular palladium-mediated three-component cyclizations of substrates containing vinyl halide, olefin, and sulfonamide moieties to generate a diverse group of nitrogen heterocycles have been developed. The methodology has been applied to construction of both fused and bridged bicyclic systems. The strategy can also be used for spirocyclizations. This chemistry involves regiospecific generation of π-allylpalladium complexes via Heck reactions of vinyl halides and simple olefins, followed by nucleophilic addition of sulfonamide anions to these intermediates.

Original languageEnglish (US)
Pages (from-to)5452-5464
Number of pages13
JournalJournal of Organic Chemistry
Volume58
Issue number20
DOIs
StatePublished - Jan 1 1993

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Nitrogen Compounds
Cyclization
Sulfonamides
Alkenes
Palladium
Anions
Nitrogen
Substrates

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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Synthesis of Bicyclic Nitrogen Compounds via Tandem Intramolecular Heck Cyclization and Subsequent Trapping of Intermediate π-Allylpalladium Complexes. / Harris, G. Davis; Herr, R. Jason; Weinreb, Steven M.

In: Journal of Organic Chemistry, Vol. 58, No. 20, 01.01.1993, p. 5452-5464.

Research output: Contribution to journalArticle

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