Pd/light-accelerated atom-transfer carbonylation of alkyl iodides: Applications in multicomponent coupling processes leading to functionalized carboxylic acid derivatives

Akira Fusano, Shuhei Sumino, Satoshi Nishitani, Takaya Inouye, Keisuke Morimoto, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

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/hv 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 [Pd 2(CNMe) 6][PF 6] 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. Light, camera, ATCion: Atom-transfer carbonylation of alkyl iodides to afford carboxylic acid esters was accelerated by the addition of transition-metal catalysts under photoirradiation. The carbonylation step proceeded through a radical mechanism.

Original languageEnglish
Pages (from-to)9415-9422
Number of pages8
JournalChemistry - A European Journal
Volume18
Issue number30
DOIs
StatePublished - 23 Jul 2012

Keywords

  • carbon monoxide
  • carbonylation
  • multicomponent reactions
  • palladium
  • radical reactions

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