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Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines

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Details

Original languageEnglish
Pages (from-to)1402-1406
Number of pages5
JournalOrganic Letters
Volume21
Issue number5
DOIs
Publication statusPublished - 15 Feb 2019
Publication typeA1 Journal article-refereed

Abstract

A new metal-free reductive amination protocol using a pinacol-derived chlorohydrosilane/pyridine system for the preparation of aminoalkylphenols is described. This method is selective toward iminiums derived from alkylphenol ketones under an in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by computational studies. This method demonstrated high functional group tolerance affording an array of novel aminoalkylphenols in moderate to high yields with equimolar amounts of reactants and a wide substrate scope.

Publication forum classification

Field of science, Statistics Finland