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Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane

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Details

Original languageEnglish
Pages (from-to)2910-2917
JournalEuropean Journal of Organic Chemistry
Volume2018
Issue number23
DOIs
Publication statusPublished - 1 Jun 2018
Publication typeA1 Journal article-refereed

Abstract

A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51–97 %). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3‐Dimethyl‐3,4,5,6‐tetrahydro‐2(1H)‐pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal‐free reduction, promoting the regio‐ and chemoselective reduction of aldehydes in ortho‐position to phenols, despite the presence of vicinal ketones. The performance of pinacol‐derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well‐established commercially available chlorohydrosilanes.

Publication forum classification

Field of science, Statistics Finland