Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature

Qiong Li; Shu Yu Zhang; Gang He; Zhaoyan Ai; William A. Nack; Gong Chen

doi:10.1021/ol500464x

Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature

Qiong Li
, Shu Yu Zhang
, Gang He
, Zhaoyan Ai
, William A. Nack
, Gong Chen

Chemistry

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

187 Scopus citations

Abstract

In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.

Original language	English (US)
Pages (from-to)	1764-1767
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	6
DOIs	https://doi.org/10.1021/ol500464x
State	Published - Mar 21 2014

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol500464x

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abstract = "In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.",

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AU - Li, Qiong

AU - Zhang, Shu Yu

AU - He, Gang

AU - Ai, Zhaoyan

AU - Nack, William A.

AU - Chen, Gong

PY - 2014/3/21

Y1 - 2014/3/21

N2 - In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.

AB - In this report, a highly efficient method for the room temperature installation of alkyl amino motifs onto the ortho position of anilines via Cu-catalyzed carboxamide-directed amination with alkylamines is described. This method offers a practical solution for the rapid synthesis of complex arylamines from simple starting materials and enables new planning strategies for the construction of arylamine-containing pharmacophores. A single electron transfer (SET)-mediated mechanism is proposed.

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U2 - 10.1021/ol500464x

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AN - SCOPUS:84896922270

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JO - Organic Letters

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ER -

Copper-catalyzed carboxamide-directed ortho amination of anilines with alkylamines at room temperature

Abstract

All Science Journal Classification (ASJC) codes

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