Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs' catalysts

Sandra M. Rountree; Sarah F.R. Taylor; Christopher Hardacre; M. Cristina Lagunas; Paul N. Davey

doi:10.1016/j.apcata.2014.08.032

Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs' catalysts

Sandra M. Rountree
, Sarah F.R. Taylor
, Christopher Hardacre
, M. Cristina Lagunas
, Paul N. Davey

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

7 Citations (Scopus)

Abstract

A series of α,β-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs' catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest, as it has not previously being used as a substrate in cross-metathesis reactions and allows access to valuable intermediates for the synthesis of new fragrances. Most reactions gave good selectivity of the desired CM product (≥90%). Detailed optimisation and mechanistic studies have been performed on the cross-metathesis of acrolein with 1-decene. Recycling of the catalyst has been attempted using ionic liquids.

Original language	English
Pages (from-to)	94-104
Number of pages	11
Journal	Applied Catalysis A: General
Volume	486
DOIs	https://doi.org/10.1016/j.apcata.2014.08.032
Publication status	Published (in print/issue) - 22 Sept 2014

Bibliographical note

Funding Information:
The authors acknowledge support from QUILL. S.M.R. acknowledges support from the Department of Education and Learning in Northern Ireland and Givaudan SA. The authors thank Dominique Lelievre and Alain Alchenberger (Givaudan SA) for odour assessments.

Publisher Copyright:
© 2014 Elsevier B.V. All rights reserved.

Funding

The authors acknowledge support from QUILL. S.M.R. acknowledges support from the Department of Education and Learning in Northern Ireland and Givaudan SA. The authors thank Dominique Lelievre and Alain Alchenberger (Givaudan SA) for odour assessments.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Acrolein
Cross-metathesis
Fragrances
Grubbs' catalysts

Access to Document

10.1016/j.apcata.2014.08.032

Cite this

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title = "Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs' catalysts",

abstract = "A series of α,β-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs' catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest, as it has not previously being used as a substrate in cross-metathesis reactions and allows access to valuable intermediates for the synthesis of new fragrances. Most reactions gave good selectivity of the desired CM product (≥90\%). Detailed optimisation and mechanistic studies have been performed on the cross-metathesis of acrolein with 1-decene. Recycling of the catalyst has been attempted using ionic liquids.",

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author = "Rountree, \{Sandra M.\} and Taylor, \{Sarah F.R.\} and Christopher Hardacre and Lagunas, \{M. Cristina\} and Davey, \{Paul N.\}",

note = "Funding Information: The authors acknowledge support from QUILL. S.M.R. acknowledges support from the Department of Education and Learning in Northern Ireland and Givaudan SA. The authors thank Dominique Lelievre and Alain Alchenberger (Givaudan SA) for odour assessments. Publisher Copyright: {\textcopyright} 2014 Elsevier B.V. All rights reserved.",

year = "2014",

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doi = "10.1016/j.apcata.2014.08.032",

language = "English",

volume = "486",

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journal = "Applied Catalysis A: General",

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AU - Rountree, Sandra M.

AU - Taylor, Sarah F.R.

AU - Hardacre, Christopher

AU - Lagunas, M. Cristina

AU - Davey, Paul N.

N1 - Funding Information: The authors acknowledge support from QUILL. S.M.R. acknowledges support from the Department of Education and Learning in Northern Ireland and Givaudan SA. The authors thank Dominique Lelievre and Alain Alchenberger (Givaudan SA) for odour assessments. Publisher Copyright: © 2014 Elsevier B.V. All rights reserved.

PY - 2014/9/22

Y1 - 2014/9/22

N2 - A series of α,β-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs' catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest, as it has not previously being used as a substrate in cross-metathesis reactions and allows access to valuable intermediates for the synthesis of new fragrances. Most reactions gave good selectivity of the desired CM product (≥90%). Detailed optimisation and mechanistic studies have been performed on the cross-metathesis of acrolein with 1-decene. Recycling of the catalyst has been attempted using ionic liquids.

AB - A series of α,β-unsaturated aldehydes and nitriles of significant interest in the fragrance industry have been prepared using Grubbs' catalysts in cross-metathesis reactions of electron-deficient olefins (i.e., acrolein, crotonaldehyde, methacrolein, and acrylonitrile) with various 1-alkenes, including 1-decene, 1-octene, 1-hexene and 2-allyloxy-6-methylheptane. The latter is of particular interest, as it has not previously being used as a substrate in cross-metathesis reactions and allows access to valuable intermediates for the synthesis of new fragrances. Most reactions gave good selectivity of the desired CM product (≥90%). Detailed optimisation and mechanistic studies have been performed on the cross-metathesis of acrolein with 1-decene. Recycling of the catalyst has been attempted using ionic liquids.

KW - Acrolein

KW - Cross-metathesis

KW - Fragrances

KW - Grubbs' catalysts

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DO - 10.1016/j.apcata.2014.08.032

M3 - Article

AN - SCOPUS:84930865119

SN - 0926-860X

VL - 486

SP - 94

EP - 104

JO - Applied Catalysis A: General

JF - Applied Catalysis A: General

ER -

Synthesis of α,β-unsaturated aldehydes and nitriles via cross-metathesis reactions using Grubbs' catalysts

Abstract

Bibliographical note

Funding

UN SDGs

Keywords

Access to Document

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