A Simple and Convenient Method for the Synthesis of N,N-Diaryl Tertiary Amines

Francis S. Wekesa; Neha Phadke; Claire Jahier; David B. Cordes; Michael Findlater

doi:10.1055/s-0033-1340820

A Simple and Convenient Method for the Synthesis of N,N-Diaryl Tertiary Amines

Francis S. Wekesa, Neha Phadke, Claire Jahier, David B. Cordes, Michael Findlater^*

^*Corresponding author for this work

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

Abstract

Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require the use of transition-metal catalysts or functional-group-intolerant hydride reductants.

Original language	English
Pages (from-to)	1046-1051
Number of pages	6
Journal	Synthesis
Volume	46
Issue number	8
DOIs	https://doi.org/10.1055/s-0033-1340820
Publication status	Published - Apr 2014

Keywords

tertiary amines
DIPEA
alkylation
benzyl halides
ARYL CHLORIDES
ALKYL-HALIDES
SECONDARY-AMINES
N-ALKYLATION
REDUCTION
AMINATION
AMIDES
CATALYSTS
EFFICIENT
COMPLEX

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title = "A Simple and Convenient Method for the Synthesis of N,N-Diaryl Tertiary Amines",

abstract = "Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require the use of transition-metal catalysts or functional-group-intolerant hydride reductants.",

keywords = "tertiary amines, DIPEA, alkylation, benzyl halides, ARYL CHLORIDES, ALKYL-HALIDES, SECONDARY-AMINES, N-ALKYLATION, REDUCTION, AMINATION, AMIDES, CATALYSTS, EFFICIENT, COMPLEX",

author = "Wekesa, \{Francis S.\} and Neha Phadke and Claire Jahier and Cordes, \{David B.\} and Michael Findlater",

year = "2014",

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doi = "10.1055/s-0033-1340820",

language = "English",

volume = "46",

pages = "1046--1051",

journal = "Synthesis",

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publisher = "Georg Thieme Verlag",

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T1 - A Simple and Convenient Method for the Synthesis of N,N-Diaryl Tertiary Amines

AU - Wekesa, Francis S.

AU - Phadke, Neha

AU - Jahier, Claire

AU - Cordes, David B.

AU - Findlater, Michael

PY - 2014/4

Y1 - 2014/4

N2 - Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require the use of transition-metal catalysts or functional-group-intolerant hydride reductants.

AB - Direct preparation of tertiary amines in which two substituents are aromatic is described. In the presence of either the inorganic base sodium tert-butoxide or the sterically hindered organic base diisopropylethylamine, the alkylation of secondary diarylamines is achieved smoothly. In contrast to methods previously reported in the literature, this procedure is high-yielding and does not require the use of transition-metal catalysts or functional-group-intolerant hydride reductants.

KW - tertiary amines

KW - DIPEA

KW - alkylation

KW - benzyl halides

KW - ARYL CHLORIDES

KW - ALKYL-HALIDES

KW - SECONDARY-AMINES

KW - N-ALKYLATION

KW - REDUCTION

KW - AMINATION

KW - AMIDES

KW - CATALYSTS

KW - EFFICIENT

KW - COMPLEX

UR - https://www.scopus.com/pages/publications/84897979152

U2 - 10.1055/s-0033-1340820

DO - 10.1055/s-0033-1340820

M3 - Article

SN - 0039-7881

VL - 46

SP - 1046

EP - 1051

JO - Synthesis

JF - Synthesis

IS - 8

ER -

A Simple and Convenient Method for the Synthesis of N,N-Diaryl Tertiary Amines

Abstract

Keywords

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