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

Synthesis, Table of Contents

Synthesis 2014; 46(08): 1046-1051
DOI: 10.1055/s-0033-1340820

practical synthetic procedures

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

Francis S. Wekesa

Texas Tech University, Department of Chemistry & Biochemistry, Lubbock, TX 79409, USA Fax: +1(806)7421289 Email: Michael.Findlater@ttu.edu

,

Neha Phadke

Texas Tech University, Department of Chemistry & Biochemistry, Lubbock, TX 79409, USA Fax: +1(806)7421289 Email: Michael.Findlater@ttu.edu

,

Claire Jahier

Texas Tech University, Department of Chemistry & Biochemistry, Lubbock, TX 79409, USA Fax: +1(806)7421289 Email: Michael.Findlater@ttu.edu

,

David B. Cordes

Texas Tech University, Department of Chemistry & Biochemistry, Lubbock, TX 79409, USA Fax: +1(806)7421289 Email: Michael.Findlater@ttu.edu

,

Michael Findlater*

Texas Tech University, Department of Chemistry & Biochemistry, Lubbock, TX 79409, USA Fax: +1(806)7421289 Email: Michael.Findlater@ttu.edu

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Abstract

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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.

Key words

tertiary amines - DIPEA - alkylation - benzyl halides

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References

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