Analogs of Grubbs' second generation catalyst with hydrophilic phosphine ligands

Phase transfer activation of ring closing alkene metathesis

Zhenxing Xi, Hassan S. Bazzi, John A. Gladysz

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Analogs of Grubbs' second generation catalyst with hydrophilic phosphine ligands are synthesized, and those with Cy2PCH2CH 2N(CH3)3 + Cl- and Cy 2PCHCH2CH2N(CH3)2 +CH2CH2 Cl- give much faster ring closing metatheses under CH2Cl2/aqueous or CH 2Cl2/aqueous HCl biphasic as opposed to CH 2Cl2 monophasic conditions. This is attributed to rapid phase transfer of the dissociated ligand to the aqueous phase, where under acidic conditions it is protonated.

Original languageEnglish
Pages (from-to)6188-6191
Number of pages4
JournalOrganic Letters
Volume13
Issue number23
DOIs
Publication statusPublished - 2 Dec 2011

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phosphine
metathesis
Alkenes
closing
phosphines
alkenes
Chemical activation
activation
methylidyne
analogs
Ligands
catalysts
ligands
Catalysts
rings

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Analogs of Grubbs' second generation catalyst with hydrophilic phosphine ligands : Phase transfer activation of ring closing alkene metathesis. / Xi, Zhenxing; Bazzi, Hassan S.; Gladysz, John A.

In: Organic Letters, Vol. 13, No. 23, 02.12.2011, p. 6188-6191.

Research output: Contribution to journalArticle

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