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

Francis 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 Wekesa, Neha Phadke, Claire Jahier, David B Cordes, Michael Findlater

Chemistry and Biochemistry

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

6 Scopus citations

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
Article number	SS-2013-M0839-PSP
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
State	Published - Apr 2014

Keywords

DIPEA
alkylation
benzyl halides
tertiary amines

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10.1055/s-0033-1340820

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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.",

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AU - Wekesa, Francis

AU - Phadke, Neha

AU - Jahier, Claire

AU - Cordes, David B

AU - Findlater, Michael

PY - 2014/4

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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 - DIPEA

KW - alkylation

KW - benzyl halides

KW - tertiary amines

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U2 - 10.1055/s-0033-1340820

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ER -

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

Abstract

Keywords

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