Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 7, Pages 2365-2368Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo010839c
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- NCI NIH HHS [1PO1 CA78048] Funding Source: Medline
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We report here a general synthetic methodology for palladium-catalyzed carbonylative annulation of o-alkynylphenol to construct 2-substituted-3-aroyl-benzo[b]furan. On the basis of the results, this methodology could be applied to a wider selection of iodide substrates to generate desired products. In accordance with mechanistic studies, this process involves coordination of cationic and less hindered acyl palladium complexes with o-alkynylphenols to create a desired cascade triad (coordination, nucleophilic addition, and reductive elimination). Consistent with this mechanism, addition of 1 equiv of AgBF4 to palladium catalyst Pd(Ph3P)(4) generates an ideal candidate for this unique transformation.
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