Synthesis of Secondary Arylamines through Copper-Mediated Intermolecular Aryl Amination

Kentaro Okano; Hidetoshi Tokuyama; Tohru Fukuyama

doi:10.1021/ol035942y

Synthesis of Secondary Arylamines through Copper-Mediated Intermolecular Aryl Amination

Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

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

148 Citations (Scopus)

Abstract

(Equation presented) A mild intermolecular copper-mediated amination of aryl iodides has been developed. The reaction takes place at room temperature or heating at 90°C and tolerates halogens attached to the aromatic ring. Its synthetic applications include a synthetic protocol for unsymmetrical N,N′-dialkylated phenylenediamines and both a stepwise and a general synthetic method for N-aryl secondary amines via Ns-anilides (readily obtained by reaction of the Ns-amide).

Original language	English
Pages (from-to)	4987-4990
Number of pages	4
Journal	Organic letters
Volume	5
Issue number	26
DOIs	https://doi.org/10.1021/ol035942y
Publication status	Published - 2003 Dec 25
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of Secondary Arylamines through Copper-Mediated Intermolecular Aryl Amination",

abstract = "(Equation presented) A mild intermolecular copper-mediated amination of aryl iodides has been developed. The reaction takes place at room temperature or heating at 90°C and tolerates halogens attached to the aromatic ring. Its synthetic applications include a synthetic protocol for unsymmetrical N,N′-dialkylated phenylenediamines and both a stepwise and a general synthetic method for N-aryl secondary amines via Ns-anilides (readily obtained by reaction of the Ns-amide).",

author = "Kentaro Okano and Hidetoshi Tokuyama and Tohru Fukuyama",

year = "2003",

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doi = "10.1021/ol035942y",

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AU - Okano, Kentaro

AU - Tokuyama, Hidetoshi

AU - Fukuyama, Tohru

PY - 2003/12/25

Y1 - 2003/12/25

N2 - (Equation presented) A mild intermolecular copper-mediated amination of aryl iodides has been developed. The reaction takes place at room temperature or heating at 90°C and tolerates halogens attached to the aromatic ring. Its synthetic applications include a synthetic protocol for unsymmetrical N,N′-dialkylated phenylenediamines and both a stepwise and a general synthetic method for N-aryl secondary amines via Ns-anilides (readily obtained by reaction of the Ns-amide).

AB - (Equation presented) A mild intermolecular copper-mediated amination of aryl iodides has been developed. The reaction takes place at room temperature or heating at 90°C and tolerates halogens attached to the aromatic ring. Its synthetic applications include a synthetic protocol for unsymmetrical N,N′-dialkylated phenylenediamines and both a stepwise and a general synthetic method for N-aryl secondary amines via Ns-anilides (readily obtained by reaction of the Ns-amide).

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