A General Method for Nucleophilic Aromatic Substitution of Aryl Fluorides and Chlorides with Dimethylamine using Hydroxide-Assisted Decomposition of N,N-Dimethylforamide.
A practical and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide assisted, thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products range from 44 - 98%, with the majority being greater than 70% for seventeen examples.
Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.
Juana
J
Garcia
Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.
Jacob
J
Sorrentino
Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.
Emily J
EJ
Diller
Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.
Daniel
D
Chapman
Department of Physical and Life Sciences, Nevada State College, Henderson, NV 89002.
Zachary R
ZR
Woydziak
DMF decomposition; Nucleophilic Aromatic Substitution; aniline derivatives; aryl halides; dimethylamine
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