Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations

Huan Zhang; Hiroki Tanimoto; Tsumoru Morimoto; Yasuhiro Nishiyama; Kiyomi Kakiuchi

doi:10.1021/ol402387w

Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations

Huan Zhang, Hiroki Tanimoto, Tsumoru Morimoto^*, Yasuhiro Nishiyama, Kiyomi Kakiuchi

^*Corresponding author for this work

Biorecognition Chemistry

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

83 Scopus citations

Abstract

Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.

Original language	English
Pages (from-to)	5222-5225
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	20
DOIs	https://doi.org/10.1021/ol402387w
State	Published - 2013/10/18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol402387w

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title = "Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations",

abstract = "Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.",

author = "Huan Zhang and Hiroki Tanimoto and Tsumoru Morimoto and Yasuhiro Nishiyama and Kiyomi Kakiuchi",

year = "2013",

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day = "18",

doi = "10.1021/ol402387w",

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T1 - Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations

AU - Zhang, Huan

AU - Tanimoto, Hiroki

AU - Morimoto, Tsumoru

AU - Nishiyama, Yasuhiro

AU - Kakiuchi, Kiyomi

PY - 2013/10/18

Y1 - 2013/10/18

N2 - Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.

AB - Regioselective rapid triazole syntheses at low temperature are described. Organic azides and propargyl cations generated by acids gave fully substituted 1H-1,2,3-triazoles. Most reactions could be performed in 5 min at not only rt but also -90 C. Both terminal and internal alkynes were acceptable, and the sterically bulky substituents could afford the products smoothly. Various types of three-component coupling reactions were demonstrated, and the presence of allenylaminodiazonium intermediates was indicated.

UR - http://www.scopus.com/inward/record.url?scp=84886248413&partnerID=8YFLogxK

U2 - 10.1021/ol402387w

DO - 10.1021/ol402387w

M3 - 学術論文

AN - SCOPUS:84886248413

SN - 1523-7060

VL - 15

SP - 5222

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Regioselective rapid synthesis of fully substituted 1,2,3-triazoles mediated by propargyl cations

Abstract

ASJC Scopus subject areas

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