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A General Method for Nucleophilic Aromatic Substitution of Aryl Fluorides and Chlorides with Dimethylamine using Hydroxide-Assisted Decomposition of N,N-Dimethylforamide.

ABSTRACT: 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.

SUBMITTER: Garcia J

PROVIDER: S-EPMC5036528 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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A General Method for Nucleophilic Aromatic Substitution of Aryl Fluorides and Chlorides with Dimethylamine using Hydroxide-Assisted Decomposition of N,N-Dimethylforamide.

Garcia Juana J Sorrentino Jacob J Diller Emily J EJ Chapman Daniel D Woydziak Zachary R ZR

Synthetic communications 20160209 5

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 ...[more]

PMID: 27688484

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