Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes

Hongying Zhou; E. Joseph Campbell; Son Binh T. Nguyen

doi:10.1021/ol0161110

Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes

Hongying Zhou, E. Joseph Campbell, Son Binh T. Nguyen^*

^*Corresponding author for this work

Chemistry

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

55 Scopus citations

Abstract

(Matrix presented) Imidazolinium salts and their N-heterocyclic carbene (NHC) derivatives catalyze the alkylation of a variety of meso epoxides in the presence of triethylaluminum (yield = 70-90%), under mild conditions. Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization side reactions under extended reaction time. Preformed NHC·AIEt₃ complexes and Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.

Original language	English (US)
Pages (from-to)	2229-2231
Number of pages	3
Journal	Organic Letters
Volume	3
Issue number	14
DOIs	https://doi.org/10.1021/ol0161110
State	Published - Jul 12 2001

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes",

abstract = "(Matrix presented) Imidazolinium salts and their N-heterocyclic carbene (NHC) derivatives catalyze the alkylation of a variety of meso epoxides in the presence of triethylaluminum (yield = 70-90%), under mild conditions. Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization side reactions under extended reaction time. Preformed NHC·AIEt3 complexes and Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.",

author = "Hongying Zhou and Campbell, {E. Joseph} and Nguyen, {Son Binh T.}",

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AU - Zhou, Hongying

AU - Campbell, E. Joseph

AU - Nguyen, Son Binh T.

PY - 2001/7/12

Y1 - 2001/7/12

N2 - (Matrix presented) Imidazolinium salts and their N-heterocyclic carbene (NHC) derivatives catalyze the alkylation of a variety of meso epoxides in the presence of triethylaluminum (yield = 70-90%), under mild conditions. Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization side reactions under extended reaction time. Preformed NHC·AIEt3 complexes and Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.

AB - (Matrix presented) Imidazolinium salts and their N-heterocyclic carbene (NHC) derivatives catalyze the alkylation of a variety of meso epoxides in the presence of triethylaluminum (yield = 70-90%), under mild conditions. Imidazolinium salts are better catalysts than their NHC derivatives but can lead to dimerization side reactions under extended reaction time. Preformed NHC·AIEt3 complexes and Wanzlick-type olefins, which are dimers of free NHCs, are also catalysts for this reaction.

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Imidazolinium salts as catalysts for the ring-opening alkylation of meso epoxides by alkylaluminum complexes

Abstract

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