Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions

Takafumi Baba; Shunsuke Takahashi; Yui Kambara; Akira Yoshimura; Victor N. Nemykin; Viktor Zhdankin; Akio Saito

doi:10.1002/adsc.201700934

Development of Imino-λ³-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions

Takafumi Baba, Shunsuke Takahashi, Yui Kambara, Akira Yoshimura, Victor N. Nemykin, Viktor Zhdankin, Akio Saito

Chemistry & Biochemistry

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

18 Scopus citations

Abstract

Aiming at the enhancement of electrophilicity of imino-λ³-iodanes, we have developed (tosylimino)pentafluorophenyl-λ³-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ³-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).

Original language	English (US)
Pages (from-to)	3860-3864
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	359
Issue number	21
DOIs	https://doi.org/10.1002/adsc.201700934
State	Published - Nov 10 2017

Bibliographical note

Funding Information:
This work was partially supported by JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15 K07852), by the Asahi Glass Foundation and by the Takeda Science Foundation. V.V.Z. is also thankful to the National Science Foundation (CHE-1262479).

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Alkynes
cycloaddition
imidazoles
iminoiodanes
metal-free

Publisher link

10.1002/adsc.201700934

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Cite this

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title = "Development of Imino-λ3-iodanes with Improved Reactivity for Metal-Free [2+2+1] Cycloaddition-Type Reactions",

abstract = "Aiming at the enhancement of electrophilicity of imino-λ3-iodanes, we have developed (tosylimino)pentafluorophenyl-λ3-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ3-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).",

keywords = "Alkynes, cycloaddition, imidazoles, iminoiodanes, metal-free",

author = "Takafumi Baba and Shunsuke Takahashi and Yui Kambara and Akira Yoshimura and Nemykin, {Victor N.} and Viktor Zhdankin and Akio Saito",

note = "Funding Information: This work was partially supported by JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15 K07852), by the Asahi Glass Foundation and by the Takeda Science Foundation. V.V.Z. is also thankful to the National Science Foundation (CHE-1262479). Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Baba, Takafumi

AU - Takahashi, Shunsuke

AU - Kambara, Yui

AU - Yoshimura, Akira

AU - Nemykin, Victor N.

AU - Zhdankin, Viktor

AU - Saito, Akio

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PY - 2017/11/10

Y1 - 2017/11/10

N2 - Aiming at the enhancement of electrophilicity of imino-λ3-iodanes, we have developed (tosylimino)pentafluorophenyl-λ3-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ3-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).

AB - Aiming at the enhancement of electrophilicity of imino-λ3-iodanes, we have developed (tosylimino)pentafluorophenyl-λ3-iodane, which shows superior reactivity compared to the commonly used (tosylimino)phenyl-λ3-iodane in the [2+2+1]-type synthesis of imidazoles. (Figure presented.).

KW - Alkynes

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KW - iminoiodanes

KW - metal-free

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