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

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Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines. / Assoah, Benedicta; Veiros, Luis F.; R. Candeias, Nuno.

In: Organic Letters, Vol. 21, No. 5, 15.02.2019, p. 1402-1406.

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@article{beb01ae565604203a0b0bc90e25690a2,
title = "Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines",
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",
year = "2019",
month = "2",
day = "15",
doi = "10.1021/acs.orglett.9b00121",
language = "English",
volume = "21",
pages = "1402--1406",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "5",

}

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TY - JOUR

T1 - Pinacol-Derived Chlorohydrosilane in Metal-Free Reductive Amination for the Preparation of Tertiary Alkylphenolmethyl Amines

AU - Assoah, Benedicta

AU - Veiros, Luis F.

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.

U2 - 10.1021/acs.orglett.9b00121

DO - 10.1021/acs.orglett.9b00121

M3 - Article

VL - 21

SP - 1402

EP - 1406

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 5

ER -