Palladium-catalyzed carbonylative annulation of o-alkynylphenols:: Syntheses of 2-substituted-3-aroyl-benzo[b]furans

被引：97

作者：

Hu, Y ^{[1
]}

Zhang, Y ^{[1
]}

Yang, Z ^{[1
]}

Fathi, R ^{[1
]}

机构：

[1] Harvard Univ, Sch Med, Inst Chem & Cell Biol, Boston, MA 02115 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 07期

关键词：

D O I：

10.1021/jo010839c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2365 / 2368

页数：4

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