N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

G A  Grasa; R M  Kissling; Steven Patrick Nolan

doi:10.1021/ol0264760

N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

G A Grasa, R M Kissling, Steven Patrick Nolan

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

Abstract

[GRAPHICS]

Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.

Original language	English
Pages (from-to)	3583-3586
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	21
DOIs	https://doi.org/10.1021/ol0264760
Publication status	Published - 17 Oct 2002

Keywords

HIGHLY SELECTIVE ACYLATION
ALCOHOLS
ANHYDRIDES
TRIFLUOROMETHANESULFONATE
ESTERS
ACID

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10.1021/ol0264760

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title = "N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions",

abstract = "[GRAPHICS]Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.",

keywords = "HIGHLY SELECTIVE ACYLATION, ALCOHOLS, ANHYDRIDES, TRIFLUOROMETHANESULFONATE, ESTERS, ACID",

author = "Grasa, {G A} and Kissling, {R M} and Nolan, {Steven Patrick}",

year = "2002",

month = oct,

day = "17",

doi = "10.1021/ol0264760",

language = "English",

volume = "4",

pages = "3583--3586",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society (ACS)",

number = "21",

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TY - JOUR

T1 - N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

AU - Grasa, G A

AU - Kissling, R M

AU - Nolan, Steven Patrick

PY - 2002/10/17

Y1 - 2002/10/17

N2 - [GRAPHICS]Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.

AB - [GRAPHICS]Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.

KW - HIGHLY SELECTIVE ACYLATION

KW - ALCOHOLS

KW - ANHYDRIDES

KW - TRIFLUOROMETHANESULFONATE

KW - ESTERS

KW - ACID

U2 - 10.1021/ol0264760

DO - 10.1021/ol0264760

M3 - Article

SN - 1523-7060

VL - 4

SP - 3583

EP - 3586

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

Abstract

Keywords

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