An Efficient Approach to Functionalized Indoles from λ 3 ‐Iodanes via Acyloxylation and Acyl Transfer

Versatile role of λ 3 ‐iodanes has been identified between the reaction of hydroquinone and β‐enaminones for the synthesis of 5‐acyloxy‐4‐hydroxy indoles. The reaction is proposed to proceed through an intermolecular C−C bond formation, intramolecular cyclization, acyloxylation and 1,4‐acyl migratio...

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Published in:Advanced synthesis & catalysis 2020-07, Vol.362 (14), p.2911-2920
Main Authors: Jeyakannu, Palaniraja, Chandru Senadi, Gopal, Chiang, Chun‐Hsien, Kumar Dhandabani, Ganesh, Chang, Yu‐Ching, Wang, Jeh‐Jeng
Format: Article
Language:English
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Summary:Versatile role of λ 3 ‐iodanes has been identified between the reaction of hydroquinone and β‐enaminones for the synthesis of 5‐acyloxy‐4‐hydroxy indoles. The reaction is proposed to proceed through an intermolecular C−C bond formation, intramolecular cyclization, acyloxylation and 1,4‐acyl migration. The important features of this work include various acyloxylation from λ 3 ‐iodanes and broad functional group tolerance to deliver 34 examples in moderate to good yields. magnified image
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000402