Metal-Free [2+2+1] annulation of alkynes, nitriles and nitrogen atoms from iminoiodanes for synthesis of highly substituted imidazoles

Akio Saito; Yui Kambara; Takuma Yagyu; Keiichi Noguchi; Akira Yoshimura; Viktor V. Zhdankin

doi:10.1002/adsc.201500032

Metal-Free [2+2+1] annulation of alkynes, nitriles and nitrogen atoms from iminoiodanes for synthesis of highly substituted imidazoles

Akio Saito, Yui Kambara, Takuma Yagyu, Keiichi Noguchi, Akira Yoshimura, Viktor V. Zhdankin

Chemistry & Biochemistry

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

38 Scopus citations

Abstract

Boron trifluoride nitrile complexes promote oxidative [2+2+1] annulations of alkynes, nitriles and N-atoms from iminoiodanes to give the corresponding 2,4-disubstituted and 2,4,5-trisubstituted N-tosylimidazoles in moderate to good yields with high regioselectivities.

Original language	English (US)
Pages (from-to)	667-671
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	357
Issue number	4
DOIs	https://doi.org/10.1002/adsc.201500032
State	Published - Mar 9 2015

Bibliographical note

Publisher Copyright:
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

alkynes
annulation
iminoiodanes
metal-free conditions
nitriles

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10.1002/adsc.201500032

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title = "Metal-Free [2+2+1] annulation of alkynes, nitriles and nitrogen atoms from iminoiodanes for synthesis of highly substituted imidazoles",

abstract = "Boron trifluoride nitrile complexes promote oxidative [2+2+1] annulations of alkynes, nitriles and N-atoms from iminoiodanes to give the corresponding 2,4-disubstituted and 2,4,5-trisubstituted N-tosylimidazoles in moderate to good yields with high regioselectivities.",

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author = "Akio Saito and Yui Kambara and Takuma Yagyu and Keiichi Noguchi and Akira Yoshimura and Zhdankin, {Viktor V.}",

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T1 - Metal-Free [2+2+1] annulation of alkynes, nitriles and nitrogen atoms from iminoiodanes for synthesis of highly substituted imidazoles

AU - Saito, Akio

AU - Kambara, Yui

AU - Yagyu, Takuma

AU - Noguchi, Keiichi

AU - Yoshimura, Akira

AU - Zhdankin, Viktor V.

PY - 2015/3/9

Y1 - 2015/3/9

N2 - Boron trifluoride nitrile complexes promote oxidative [2+2+1] annulations of alkynes, nitriles and N-atoms from iminoiodanes to give the corresponding 2,4-disubstituted and 2,4,5-trisubstituted N-tosylimidazoles in moderate to good yields with high regioselectivities.

AB - Boron trifluoride nitrile complexes promote oxidative [2+2+1] annulations of alkynes, nitriles and N-atoms from iminoiodanes to give the corresponding 2,4-disubstituted and 2,4,5-trisubstituted N-tosylimidazoles in moderate to good yields with high regioselectivities.

KW - alkynes

KW - annulation

KW - iminoiodanes

KW - metal-free conditions

KW - nitriles

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JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

SN - 1615-4150

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ER -

Metal-Free [2+2+1] annulation of alkynes, nitriles and nitrogen atoms from iminoiodanes for synthesis of highly substituted imidazoles

Abstract

Bibliographical note

Keywords

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