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

doi:10.1021/ol202548q

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

19 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 language	English
Pages (from-to)	6188-6191
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	23
DOIs	https://doi.org/10.1021/ol202548q
Publication status	Published - 2 Dec 2011
Externally published	Yes

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title = "Analogs of Grubbs' second generation catalyst with hydrophilic phosphine ligands: Phase transfer activation of ring closing alkene metathesis",

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.",

author = "Zhenxing Xi and Bazzi, \{Hassan S.\} and Gladysz, \{John A.\}",

year = "2011",

month = dec,

day = "2",

doi = "10.1021/ol202548q",

language = "English",

volume = "13",

pages = "6188--6191",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "23",

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TY - JOUR

T1 - Analogs of Grubbs' second generation catalyst with hydrophilic phosphine ligands

T2 - Phase transfer activation of ring closing alkene metathesis

AU - Xi, Zhenxing

AU - Bazzi, Hassan S.

AU - Gladysz, John A.

PY - 2011/12/2

Y1 - 2011/12/2

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/82355190290

U2 - 10.1021/ol202548q

DO - 10.1021/ol202548q

M3 - Article

AN - SCOPUS:82355190290

SN - 1523-7060

VL - 13

SP - 6188

EP - 6191

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Analogs of Grubbs' second generation catalyst with hydrophilic phosphine ligands: Phase transfer activation of ring closing alkene metathesis

Abstract

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