A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1 H -1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide

Guang Long Wu; Qin Pei Wu

doi:10.1055/s-0037-1609720

A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1 H -1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide

Guang Long Wu^*
, Qin Pei Wu

^*Corresponding author for this work

Beijing Institute of Technology

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

24 Citations (Scopus)

Abstract

A mild and metal-free multi-component reaction to synthesize 4,5-disubstituted 1 H -1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide is described. The process undergoes an organocatalyzed coupling of formyl group with phosphonium to form a key intermediate, olefinic phosphonium salt, which is followed by the [3+2] cycloaddition of the azide to the activated alkene. A series of representative 4,5-disubstituted 1 H -1,2,3-triazoles were prepared.

Original language	English
Pages (from-to)	2768-2774
Number of pages	7
Journal	Synthesis
Volume	50
Issue number	14
DOIs	https://doi.org/10.1055/s-0037-1609720
Publication status	Published - 17 Jul 2018
Externally published	Yes

Keywords

cycloaddition
multicomponent reaction
organic catalyst
phosphonium salt
triazole

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10.1055/s-0037-1609720

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title = "A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1 H -1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide",

abstract = "A mild and metal-free multi-component reaction to synthesize 4,5-disubstituted 1 H -1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide is described. The process undergoes an organocatalyzed coupling of formyl group with phosphonium to form a key intermediate, olefinic phosphonium salt, which is followed by the [3+2] cycloaddition of the azide to the activated alkene. A series of representative 4,5-disubstituted 1 H -1,2,3-triazoles were prepared.",

keywords = "cycloaddition, multicomponent reaction, organic catalyst, phosphonium salt, triazole",

author = "Wu, \{Guang Long\} and Wu, \{Qin Pei\}",

note = "Publisher Copyright: {\textcopyright} Georg Thieme Verlag Stuttgart New York.",

year = "2018",

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day = "17",

doi = "10.1055/s-0037-1609720",

language = "English",

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journal = "Synthesis",

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T1 - A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1 H -1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide

AU - Wu, Guang Long

AU - Wu, Qin Pei

N1 - Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2018/7/17

Y1 - 2018/7/17

N2 - A mild and metal-free multi-component reaction to synthesize 4,5-disubstituted 1 H -1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide is described. The process undergoes an organocatalyzed coupling of formyl group with phosphonium to form a key intermediate, olefinic phosphonium salt, which is followed by the [3+2] cycloaddition of the azide to the activated alkene. A series of representative 4,5-disubstituted 1 H -1,2,3-triazoles were prepared.

AB - A mild and metal-free multi-component reaction to synthesize 4,5-disubstituted 1 H -1,2,3-triazoles from phosphonium salts, aldehydes, and sodium azide is described. The process undergoes an organocatalyzed coupling of formyl group with phosphonium to form a key intermediate, olefinic phosphonium salt, which is followed by the [3+2] cycloaddition of the azide to the activated alkene. A series of representative 4,5-disubstituted 1 H -1,2,3-triazoles were prepared.

KW - cycloaddition

KW - multicomponent reaction

KW - organic catalyst

KW - phosphonium salt

KW - triazole

UR - https://www.scopus.com/pages/publications/85046773498

U2 - 10.1055/s-0037-1609720

DO - 10.1055/s-0037-1609720

M3 - Article

AN - SCOPUS:85046773498

SN - 0039-7881

VL - 50

SP - 2768

EP - 2774

JO - Synthesis

JF - Synthesis

IS - 14

ER -

A Mild Multi-Component Reaction for the Synthesis of 4,5-Disubstituted 1 H -1,2,3-Triazoles from Phosphonium Salts, Aldehydes, and Sodium Azide

Abstract

Keywords

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