Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 30, Pages 9415-9422Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201200752
Keywords
carbon monoxide; carbonylation; multicomponent reactions; palladium; radical reactions
Categories
Funding
- JSPS
- MEXT Japan
- Scientific Research on Innovative Areas [2105]
- Grants-in-Aid for Scientific Research [21106003, 23350045] Funding Source: KAKEN
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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/h? reaction system, vicinal C-functionalization of alkenes was attained in which a-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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