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Substituent-Directed Regioselective Azidation: Copper-Catalyzed C-H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole

Dhineshkumar, Jayaraman and Gadde, Karthik and Prabhu, Kandikere Ramaiah (2018) Substituent-Directed Regioselective Azidation: Copper-Catalyzed C-H Azidation and Iodine-Catalyzed Dearomatizative Azidation of Indole. In: JOURNAL OF ORGANIC CHEMISTRY, 83 (1). pp. 228-235.

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Official URL: http://dx.doi.org/10.1021/acs.joc.7b02591

Abstract

Azidation of indoles using iodine and copper bromide as catalysts under ambient reaction conditions is presented. The regioselectivity is directed by the substituent at the C3-position of indole. A radical stabilizing group such as an ester or ketone moiety at the C3-position of indole leads to azidation at the C2-position, whereas a less radical stabilizing group such as an alkyl or amide group at the C3-position of indole furnishes the 3-azidooxindole product. This protocol is mild and efficient to obtain several 2-azidoindole derivatives and 3-azidooxindole derivatives in moderate to good yields. The reaction conditions hold well for gram-scale synthesis.

Item Type: Journal Article
Additional Information: Copy right for thjis article belong to the AMER CHEMICAL SOC, 1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 02 Mar 2018 15:05
Last Modified: 02 Mar 2018 15:05
URI: http://eprints.iisc.ac.in/id/eprint/58920

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