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

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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.

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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All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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