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Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles

Lanke, Veeranjaneyulu and Bettadapur, Kiran R and Prabhu, Kandikere Ramaiah (2016) Electronic Nature of Ketone Directing Group as a Key To Control C-2 vs C-4 Alkenylation of Indoles. In: ORGANIC LETTERS, 18 (21). pp. 5496-5499.

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Official URL: http://dx.doi.org/10.1021/acs.orglett.6b02698

Abstract

A novel mode of achieving site selectivity between C-2 and C-4 positions in the indole framework by altering the property of the ketone directing group is disclosed. Methyl ketone, as directing group, furnishes exclusively C-2 alkenylated product, whereas trifluoromethyl ketone changes the selectivity to C-4, indicating that the electronic nature of the directing group controls the unusual choice between a 5-membered and a 6-membered metallacycle. The screening of other carbonyl-derived directing groups reveals that strong and weak directing groups exhibit opposite selectivity. Experimental controls and deuteration experiments lend support to the proposed mechanism.

Item Type: Journal Article
Additional Information: Copy right for this article belongs 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: 04 Jan 2017 04:48
Last Modified: 04 Jan 2017 04:48
URI: http://eprints.iisc.ac.in/id/eprint/55707

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