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Revisiting the reduction of indoles by hydroboranes: A combined experimental and computational study

Jayaraman, Arumugam, Powell-Davies, Henry and Fontaine, Frédéric-Georges 2019. Revisiting the reduction of indoles by hydroboranes: A combined experimental and computational study. Tetrahedron 75 (14) , pp. 2118-2127. 10.1016/j.tet.2019.02.048

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Abstract

A combined experimental and density functional computational study was used to probe the mechanism for the reduction of indoles using simple borane BH3·DMS (DMS = dimethyl sulfide). Experimental and computational studies all steer to the formation of the reduced species 1-BH2-indolines as the resting state for this reaction, as opposed to the historically presumed formation of the unreduced 1-BH2-indoles, before the addition of a proton source to form the final product indolines. Furthermore, it was observed that molecular H2 was generated and consumed in the reaction. Computations put forward hydroboration followed by protodeborylation as the very reasonable mechanistic route for the formation of experimentally observed major intermediate 1-BH2 indolines. For the H2 consumption in the reaction, computations suggest the frustrated Lewis pair-type heterolytic splitting of H2 by a bis(3-indolinyl)borane intermediate.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4020
Date of First Compliant Deposit: 2 March 2019
Date of Acceptance: 22 February 2019
Last Modified: 13 Mar 2020 06:31
URI: http://orca.cf.ac.uk/id/eprint/120145

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