Coupling of vinylic tellurides with alkynes catalyzed by palladium dichloride: Evaluation of synthetic and mechanistic details

C. Raminelli, Martin H. G. Prechtl, L. S. Santos, M. N. Eberlin, J. V. Comasseto

Research output: Contribution to journalJournal articlepeer-review

Abstract

Under palladium dichloride catalysis, vinylic tellurides couple efficiently with alkynes with retention of the double-bond geometry. Herein we show that the amount of the PdCl2 catalyst can be reduced from 40 mol % to 10 mol % by using copper(II) chloride as an oxidizing agent. Under these conditions, an inert atmosphere is no longer required and the reaction occurs quite efficiently in the presence of air, leading to the enynes in 40-82% isolated yields. Mass and tandem mass spectrometric experiments using electrospray ionization were performed, and Pd-Te cationic intermediates were, for the first time, intercepted and transferred to the gas phase for structural characterization. An expanded catalytic cycle for this important method for enyne synthesis is proposed.
Original languageEnglish
JournalOrganometallics
Volume23
Issue number16
Pages (from-to)3990-3996
Number of pages7
ISSN0276-7333
DOIs
Publication statusPublished - 2004
Externally publishedYes

Bibliographical note

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Keywords

  • electrospray mass-spectrometry atmospheric-pressure photoionization heck reaction antiinflammatory activity organic tellurides ionization mass z-enynes arylation enediynes chemistry Chemistry

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