Revisiting the reduction of indoles by hydrobranes : a combined experimental and computational study

Authors: Jayaraman, ArumugamPowell-Davies, HenryFontaine, Frédéric-Georges
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.
Document Type: Article de recherche
Issue Date: 27 February 2019
Open Access Date: 27 February 2021
Document version: AM
This document was published in: Tetrahedron, Vol. 75 (14), 2118-2127 (2019)
Alternative version: 10.1016/j.tet.2019.02.048
Collection:Articles publiés dans des revues avec comité de lecture

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