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Catalytic Reaction of Aryldiazoacetates with Indole and Its Derivatives:Profound Effect of N-1 Substitutent on the Reaction Pathways

โœ Scribed by Xue-Jing ZHANG; Sheng-Ping LIU; Ming YAN


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
97 KB
Volume
26
Category
Article
ISSN
0256-7660

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โœฆ Synopsis


Abstract

The reaction of indole and its derivatives with aryldiazoacetates has been studied in the presence of copper and rhodium catalysts. The electronic property of Nโ€1 substitutent showed significant effect on the reaction pathways. The electronโ€donating group favored the formation of the ฮฒโ€alkylation products, while the electronโ€withdrawing group favored the formation of the cyclopropane products. A reaction mechanism was proposed based on the experimental data and previous research results. The structure of aryl group in diazo compounds also affected the yield of the ฮฒโ€alkylation products or the cyclopropane products.


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