Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters

Nageswaran Praveenganesh, Cristina De Candia, Antony Memboeuf, G. Lendvay, Yves Gimbert, Pierre Y. Chavant

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Vinylboronic esters derived from 4,4,6-trimethyl-[1,3,2]dioxaborinane react with nitrones in the presence of dimethylzinc; nucleophilic addition of the vinyl group onto nitrones produces N-allylic hydroxylamines in fair yields. The sequence is compatible with various functional groups on the vinylic moiety. The mechanism and kinetic aspects are discussed on the basis of DFT calculations.

Original languageEnglish
Pages (from-to)2447-2454
Number of pages8
JournalJournal of Organometallic Chemistry
Volume695
Issue number22
DOIs
Publication statusPublished - Oct 15 2010

Fingerprint

Discrete Fourier transforms
Functional groups
esters
Esters
Hydroxylamines
Kinetics
kinetics
nitrones
dimethylzinc

Keywords

  • Allyl-hydroxylamines
  • Boron
  • Transmetallation
  • Vinylboronates
  • Zinc

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry
  • Biochemistry

Cite this

Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters. / Praveenganesh, Nageswaran; De Candia, Cristina; Memboeuf, Antony; Lendvay, G.; Gimbert, Yves; Chavant, Pierre Y.

In: Journal of Organometallic Chemistry, Vol. 695, No. 22, 15.10.2010, p. 2447-2454.

Research output: Contribution to journalArticle

Praveenganesh, Nageswaran ; De Candia, Cristina ; Memboeuf, Antony ; Lendvay, G. ; Gimbert, Yves ; Chavant, Pierre Y. / Improved dimethylzinc-promoted vinylation of nitrones with vinylboronic esters. In: Journal of Organometallic Chemistry. 2010 ; Vol. 695, No. 22. pp. 2447-2454.
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AU - Gimbert, Yves

AU - Chavant, Pierre Y.

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