Solvent-free chelation-assisted hydroacylation of olefin by rhodium(I) catalyst under microwave irradiation

André Loupy, Saber Chatti, Sarah Delamare, Dae Yon Lee, Jong Hwa Chung, Chul Ho Jun

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A solvent-free protocol for the rhodium(I)-catalyzed intermolecular hydroacylation was achieved under microwave irradiation to furnish various ketones in high yields. The reactivity was improved by the addition of aniline as well as 2-amino-3-picoline and benzoic acid to induce a transimination, which facilitates the formation of intermediate aldimine. A comparison of the reactivity between the reaction performed under the conventional heating mode and the microwave irradiation using monomode reactor revealed an important specific microwave effect during the chelation-assisted hydroacylation. It is supposed that the observed specific microwave effect mainly originates from the formation of aldimine by condensation of aldehyde and amine, which leads to a development of charges in the transition state. This result confirms that the rate-determining step of the reaction is the initial condensation step rather than the subsequent hydroiminoacylation step.

Original languageEnglish
Pages (from-to)1280-1285
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 1
Volume10
DOIs
Publication statusPublished - 2002 Jan 1

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Rhodium
Microwave irradiation
Alkenes
Chelation
Condensation
Picolines
Microwaves
Catalysts
Benzoic Acid
Ketones
Aldehydes
Amines
Heating
aniline

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Loupy, André ; Chatti, Saber ; Delamare, Sarah ; Lee, Dae Yon ; Chung, Jong Hwa ; Jun, Chul Ho. / Solvent-free chelation-assisted hydroacylation of olefin by rhodium(I) catalyst under microwave irradiation. In: Journal of the Chemical Society. Perkin Transactions 1. 2002 ; Vol. 10. pp. 1280-1285.
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abstract = "A solvent-free protocol for the rhodium(I)-catalyzed intermolecular hydroacylation was achieved under microwave irradiation to furnish various ketones in high yields. The reactivity was improved by the addition of aniline as well as 2-amino-3-picoline and benzoic acid to induce a transimination, which facilitates the formation of intermediate aldimine. A comparison of the reactivity between the reaction performed under the conventional heating mode and the microwave irradiation using monomode reactor revealed an important specific microwave effect during the chelation-assisted hydroacylation. It is supposed that the observed specific microwave effect mainly originates from the formation of aldimine by condensation of aldehyde and amine, which leads to a development of charges in the transition state. This result confirms that the rate-determining step of the reaction is the initial condensation step rather than the subsequent hydroiminoacylation step.",
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Solvent-free chelation-assisted hydroacylation of olefin by rhodium(I) catalyst under microwave irradiation. / Loupy, André; Chatti, Saber; Delamare, Sarah; Lee, Dae Yon; Chung, Jong Hwa; Jun, Chul Ho.

In: Journal of the Chemical Society. Perkin Transactions 1, Vol. 10, 01.01.2002, p. 1280-1285.

Research output: Contribution to journalArticle

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AU - Chatti, Saber

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AB - A solvent-free protocol for the rhodium(I)-catalyzed intermolecular hydroacylation was achieved under microwave irradiation to furnish various ketones in high yields. The reactivity was improved by the addition of aniline as well as 2-amino-3-picoline and benzoic acid to induce a transimination, which facilitates the formation of intermediate aldimine. A comparison of the reactivity between the reaction performed under the conventional heating mode and the microwave irradiation using monomode reactor revealed an important specific microwave effect during the chelation-assisted hydroacylation. It is supposed that the observed specific microwave effect mainly originates from the formation of aldimine by condensation of aldehyde and amine, which leads to a development of charges in the transition state. This result confirms that the rate-determining step of the reaction is the initial condensation step rather than the subsequent hydroiminoacylation step.

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