Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

被引：40

作者：

Chan, Wai-Wing

Kwong, Tsz-Lung

Yu, Wing-Yiu ^{[1
]}

机构：

[1] Hong Kong Polytech Univ, State Key Lab Chirosci, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 18期

关键词：

C-H FUNCTIONALIZATION; SELECTIVE SYNTHESIS; OXINDOLE SYNTHESIS; CYCLOPROPANATION; INSERTION; ISOCYANATES; DIAZOACETATES; DECOMPOSITION; INHIBITORS; COMPLEXES;

D O I：

10.1039/c2ob06985g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

With [Ru(p-cymene)Cl-2](2) as catalyst, diazo-beta-ketoanilides would undergo intramolecular carbenoid arene C-H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (k(H)/k(D) similar to 1) suggests that the reaction should not proceed by rate-limiting C-H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.

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收藏

页码：3749 / 3755

页数：7

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