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Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes

Balaji, Pandur Venkatesan and Chandrasekaran, Srinivasan (2016) Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes. In: TETRAHEDRON, 72 (8). pp. 1095-1104.

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Official URL: http://dx.doi.org/10.1016/j.tet.2016.01.005


We report here the first general method for the geminal diamination and an intermolecular metal-free, geminal aminooxygenation of vinylarenes using hypervalent iodine reagent. A new m-CPBA mediated geminal aminooxygenation is also reported. A novel reagent-switch for the control of migrating group by controlling the two independent geminal addition paths is developed. Deuterium labelling studies and the control studies have provided unambiguous evidences for the phenyl migration and hydride migration in the oxidative geminal difunctionalization process mediated by Phl(OCOCF3)(2) and m-CPBA, respectively through a semi-pinacol rearrangement. (C) 2016 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Publication: TETRAHEDRON
Additional Information: Copy right for this article belongs to thePERGAMON-ELSEVIER SCIENCE LTD, THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Keywords: Geminal diamination; Geminal aminooxygenation; Hypervalent iodine; Metal-free conditions; Semi-pinacol rearrangement
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 02 Apr 2016 09:27
Last Modified: 02 Apr 2016 09:27
URI: http://eprints.iisc.ac.in/id/eprint/53461

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