N-Arylation of Tertiary Amines under Mild Conditions

Maayan Hirsch; Shubhendu Dhara; Charles E. Diesendruck

doi:10.1021/acs.orglett.6b00078

N-Arylation of Tertiary Amines under Mild Conditions

Maayan Hirsch, Shubhendu Dhara, Charles E. Diesendruck

Technion - Israel Institute of Technology

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

Abstract

A transition-metal-free procedure for the N-arylation of tertiary amines to sp³ quaternary ammonium salts is described. The presented conditions allow for the isolation of trialkylaryl, dialkyldiaryl, and novel triarylalkyl ammonium salts, including N-chiral quaternary ammonium salts. The reaction works at room temperature, open to air with electron-rich or -poor benzyne precursors and different tertiary amines, allowing the synthesis of a broad range of N-aryl ammonium salts that have applications in a variety of fields.

Original language	American English
Pages (from-to)	980-983
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.6b00078
State	Published - 4 Mar 2016

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.6b00078

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abstract = "A transition-metal-free procedure for the N-arylation of tertiary amines to sp3 quaternary ammonium salts is described. The presented conditions allow for the isolation of trialkylaryl, dialkyldiaryl, and novel triarylalkyl ammonium salts, including N-chiral quaternary ammonium salts. The reaction works at room temperature, open to air with electron-rich or -poor benzyne precursors and different tertiary amines, allowing the synthesis of a broad range of N-aryl ammonium salts that have applications in a variety of fields.",

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N2 - A transition-metal-free procedure for the N-arylation of tertiary amines to sp3 quaternary ammonium salts is described. The presented conditions allow for the isolation of trialkylaryl, dialkyldiaryl, and novel triarylalkyl ammonium salts, including N-chiral quaternary ammonium salts. The reaction works at room temperature, open to air with electron-rich or -poor benzyne precursors and different tertiary amines, allowing the synthesis of a broad range of N-aryl ammonium salts that have applications in a variety of fields.

AB - A transition-metal-free procedure for the N-arylation of tertiary amines to sp3 quaternary ammonium salts is described. The presented conditions allow for the isolation of trialkylaryl, dialkyldiaryl, and novel triarylalkyl ammonium salts, including N-chiral quaternary ammonium salts. The reaction works at room temperature, open to air with electron-rich or -poor benzyne precursors and different tertiary amines, allowing the synthesis of a broad range of N-aryl ammonium salts that have applications in a variety of fields.

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DO - 10.1021/acs.orglett.6b00078

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JO - Organic Letters

JF - Organic Letters

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N-Arylation of Tertiary Amines under Mild Conditions

Abstract

All Science Journal Classification (ASJC) codes

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