One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

Sebastien Ladouceur; Ahmed M. Soliman; Eli Zysman-Colman

doi:10.1055/s-0030-1260256

One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

Sebastien Ladouceur, Ahmed M. Soliman, Eli Zysman-Colman^*

^*Corresponding author for this work

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

Abstract

1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

Original language	English
Pages (from-to)	3604-3611
Number of pages	8
Journal	Synthesis
Issue number	22
DOIs	https://doi.org/10.1055/s-0030-1260256
Publication status	Published - Nov 2011

Keywords

click chemistry
Huisgen cycloaddition
triazoles
alkynes
azides
RHENIUM TRICARBONYL COMPLEXES
SITU GENERATED AZIDES
1,4-DISUBSTITUTED 1,2,3-TRIAZOLES
TERMINAL ALKYNES
1,3-DIPOLAR CYCLOADDITIONS
REGIOSELECTIVE SYNTHESIS
RUTHENIUM(II) COMPLEXES
IRIDIUM(III) COMPLEXES
COUPLING REACTION
LIGANDS

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@article{8381af6ef0394de8aa07800734c9f32b,

title = "One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides",

abstract = "1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.",

keywords = "click chemistry, Huisgen cycloaddition, triazoles, alkynes, azides, RHENIUM TRICARBONYL COMPLEXES, SITU GENERATED AZIDES, 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES, TERMINAL ALKYNES, 1,3-DIPOLAR CYCLOADDITIONS, REGIOSELECTIVE SYNTHESIS, RUTHENIUM(II) COMPLEXES, IRIDIUM(III) COMPLEXES, COUPLING REACTION, LIGANDS",

author = "Sebastien Ladouceur and Soliman, {Ahmed M.} and Eli Zysman-Colman",

year = "2011",

month = nov,

doi = "10.1055/s-0030-1260256",

language = "English",

pages = "3604--3611",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "22",

}

TY - JOUR

T1 - One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

AU - Ladouceur, Sebastien

AU - Soliman, Ahmed M.

AU - Zysman-Colman, Eli

PY - 2011/11

Y1 - 2011/11

N2 - 1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

AB - 1N-Alkyl-4-aryl-1,2,3-triazoles have been prepared through a multicomponent one-pot protocol from the corresponding (arylethynyl)trimethylsilanes and alkyl bromides. In situ alkyl azide formation and alkyne deprotection followed by copper(I)-catalyzed click cycloaddition afforded the desired 1,4-disubstituted 1,2,3-triazoles in generally good to excellent yield, with only minor observation of the undesired 1,5-regioisomeric cycloadduct. The protocol eliminates the need to use reactive organic azides and terminal alkynes.

KW - click chemistry

KW - Huisgen cycloaddition

KW - triazoles

KW - alkynes

KW - azides

KW - RHENIUM TRICARBONYL COMPLEXES

KW - SITU GENERATED AZIDES

KW - 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES

KW - TERMINAL ALKYNES

KW - 1,3-DIPOLAR CYCLOADDITIONS

KW - REGIOSELECTIVE SYNTHESIS

KW - RUTHENIUM(II) COMPLEXES

KW - IRIDIUM(III) COMPLEXES

KW - COUPLING REACTION

KW - LIGANDS

U2 - 10.1055/s-0030-1260256

DO - 10.1055/s-0030-1260256

M3 - Article

SN - 0039-7881

SP - 3604

EP - 3611

JO - Synthesis

JF - Synthesis

IS - 22

ER -

One-Pot Click Synthesis of 1N-Alkyl-4-aryl-1,2,3-triazoles from Protected Arylalkynes and Alkyl Bromides

Abstract

Keywords

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