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

Benedicta Assoah; Luis F. Veiros; Nuno R. Candeias

doi:10.1021/acs.orglett.9b00121

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

Benedicta Assoah
, Luis F. Veiros
, Nuno R. Candeias

Research output: Contribution to journal › Article › Scientific › peer-review

6 Citations (Scopus)

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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.

Original language	English
Pages (from-to)	1402-1406
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.9b00121
Publication status	Published - 15 Feb 2019
Publication type	A1 Journal article-refereed

Funding

The academy of Finland is acknowledged for financial support to N.R.C. (Decisions No. 326487 and 326486). We thank Joaõ R. Vale (Faculty of Engineering and Natural Sciences, TAU) for HRMS measurements. The CSC-IT center for Science Ltd., Finland, is acknowledged for the computational resources allocation. L.F.V. acknowledges Fundaca̧ õ para a Cienciâ e Tecnologia (UID/QUI/00100/2013).

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acs.orglett.9b00121
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http://urn.fi/URN:NBN:fi:tty-201906281915Licence: CC BY

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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.",

author = "Benedicta Assoah and Veiros, \{Luis F.\} and \{R. Candeias\}, Nuno",

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AU - R. Candeias, Nuno

PY - 2019/2/15

Y1 - 2019/2/15

N2 - 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.

AB - 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.

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IS - 5

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

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