1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts

Qiang Qiang Li; Yosuke Hamamoto; Cheryl Cai Hui Tan; Hiroyasu Sato; Shingo Ito

doi:10.1039/d2qo00941b

1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts

Qiang Qiang Li, Yosuke Hamamoto, Cheryl Cai Hui Tan, Hiroyasu Sato, Shingo Ito^*

^*Corresponding author for this work

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

4 Citations (Scopus)

Abstract

A new synthetic approach to π-extended imidazolium salts is developed based on 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with imidoyl chlorides, where the key to the successful conversion is the addition of cesium fluoride as an additive. Experimental and theoretical studies revealed that this cycloaddition proceeds via a stepwise mechanism rather than a concerted mechanism. This present method provides an efficient method to synthesize a variety of imidazolium-containing polycyclic aromatic compounds.

Original language	English
Pages (from-to)	4128-4134
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	9
Issue number	15
DOIs	https://doi.org/10.1039/d2qo00941b
Publication status	Published - Jun 29 2022
Externally published	Yes

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© 2022 The Royal Society of Chemistry.

ASJC Scopus Subject Areas

Organic Chemistry

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abstract = "A new synthetic approach to π-extended imidazolium salts is developed based on 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with imidoyl chlorides, where the key to the successful conversion is the addition of cesium fluoride as an additive. Experimental and theoretical studies revealed that this cycloaddition proceeds via a stepwise mechanism rather than a concerted mechanism. This present method provides an efficient method to synthesize a variety of imidazolium-containing polycyclic aromatic compounds.",

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AU - Li, Qiang Qiang

AU - Hamamoto, Yosuke

AU - Tan, Cheryl Cai Hui

AU - Sato, Hiroyasu

AU - Ito, Shingo

PY - 2022/6/29

Y1 - 2022/6/29

N2 - A new synthetic approach to π-extended imidazolium salts is developed based on 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with imidoyl chlorides, where the key to the successful conversion is the addition of cesium fluoride as an additive. Experimental and theoretical studies revealed that this cycloaddition proceeds via a stepwise mechanism rather than a concerted mechanism. This present method provides an efficient method to synthesize a variety of imidazolium-containing polycyclic aromatic compounds.

AB - A new synthetic approach to π-extended imidazolium salts is developed based on 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with imidoyl chlorides, where the key to the successful conversion is the addition of cesium fluoride as an additive. Experimental and theoretical studies revealed that this cycloaddition proceeds via a stepwise mechanism rather than a concerted mechanism. This present method provides an efficient method to synthesize a variety of imidazolium-containing polycyclic aromatic compounds.

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1,3-Dipolar cycloaddition of azomethine ylides and imidoyl halides for synthesis of π-extended imidazolium salts

Abstract

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