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

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

42 Scopus citations

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	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
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Maayan Hirsch and Shubhendu Dhara and Diesendruck, \{Charles E.\}",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

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doi = "10.1021/acs.orglett.6b00078",

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T1 - N-Arylation of Tertiary Amines under Mild Conditions

AU - Hirsch, Maayan

AU - Dhara, Shubhendu

AU - Diesendruck, Charles E.

PY - 2016/3/4

Y1 - 2016/3/4

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.

UR - https://www.scopus.com/pages/publications/84960153807

U2 - 10.1021/acs.orglett.6b00078

DO - 10.1021/acs.orglett.6b00078

M3 - Article

AN - SCOPUS:84960153807

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SP - 980

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JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

N-Arylation of Tertiary Amines under Mild Conditions

Abstract

ASJC Scopus subject areas

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