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Pd/Light-Accelerated Atom-Transfer Carbonylation of Alkyl Iodides: Applications in Multicomponent Coupling Processes Leading to Functionalized Carboxylic Acid Derivatives

Authors

  • Dr. Akira Fusano,

    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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  • Shuhei Sumino,

    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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  • Satoshi Nishitani,

    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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  • Takaya Inouye,

    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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  • Keisuke Morimoto,

    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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  • Dr. Takahide Fukuyama,

    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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  • Prof. Ilhyong Ryu

    Corresponding author
    1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
    • Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531 (Japan), Fax: (+81) 72-254-9695
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Abstract

The atom-transfer carbonylation reaction of various alkyl iodides thereby leading to carboxylic acid esters was effectively accelerated by the addition of transition-metal catalysts under photoirradiation conditions. By using a combined Pd/ reaction system, vicinal C-functionalization of alkenes was attained in which α-substituted iodoalkanes, alkenes, carbon monoxide, and alcohols were coupled to give functionalized esters. When alkenyl alcohols were used as acceptor alkenes, three-component coupling reactions, which were accompanied by intramolecular esterification, proceeded to give lactones. Pd-dimer complex [Pd2(CNMe)6][PF6]2, which is known to undergo homolysis under photoirradiation conditions, worked quite well as a catalyst in these three- or four-component coupling reactions. In this metal/radical hybrid system, both Pd radicals and acyl radicals are key players and a stereochemical study confirmed the carbonylation step proceeded through a radical carbonylation mechanism.

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