Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

Saki Uraoka; Ikumi Shinohara; Hisato Shimizu; Keiichi Noguchi; Akira Yoshimura; Viktor Zhdankin; Akio Saito

doi:10.1002/ejoc.201801340

Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

Saki Uraoka, Ikumi Shinohara, Hisato Shimizu, Keiichi Noguchi, Akira Yoshimura, Viktor Zhdankin, Akio Saito

Chemistry & Biochemistry

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

7 Scopus citations

Abstract

As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. This method can be applied to hetero Diels–Alder (HDA) reactions with dienes and ene reactions with alkenes. Furthermore, the conversions of the representative HDA adduct to nitrone and 2-amino alcohols were demonstrated. Compared with previous metal-catalyzed oxidation methods, this work provides a more efficient and environmentally friendly procedure.

Original language	English (US)
Pages (from-to)	6199-6203
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	45
DOIs	https://doi.org/10.1002/ejoc.201801340
State	Published - Dec 6 2018

Bibliographical note

Funding Information:
This work was partially supported by JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15K07852) and by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). A. Y. and V. V. Z. are thankful to Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/ 2018) and to Russian Science Foundation (RSF-16-13-10081).

Publisher Copyright:
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

Acylnitroso
Catalysis
Cycloaddition
Ene reaction
Iodine

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10.1002/ejoc.201801340

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abstract = "As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. This method can be applied to hetero Diels–Alder (HDA) reactions with dienes and ene reactions with alkenes. Furthermore, the conversions of the representative HDA adduct to nitrone and 2-amino alcohols were demonstrated. Compared with previous metal-catalyzed oxidation methods, this work provides a more efficient and environmentally friendly procedure.",

keywords = "Acylnitroso, Catalysis, Cycloaddition, Ene reaction, Iodine",

author = "Saki Uraoka and Ikumi Shinohara and Hisato Shimizu and Keiichi Noguchi and Akira Yoshimura 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 15K07852) and by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). A. Y. and V. V. Z. are thankful to Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/ 2018) and to Russian Science Foundation (RSF-16-13-10081). Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

AU - Uraoka, Saki

AU - Shinohara, Ikumi

AU - Shimizu, Hisato

AU - Noguchi, Keiichi

AU - Yoshimura, Akira

AU - Zhdankin, Viktor

AU - Saito, Akio

N1 - Funding Information: This work was partially supported by JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15K07852) and by JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199). A. Y. and V. V. Z. are thankful to Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/ 2018) and to Russian Science Foundation (RSF-16-13-10081). Publisher Copyright: © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2018/12/6

Y1 - 2018/12/6

N2 - As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. This method can be applied to hetero Diels–Alder (HDA) reactions with dienes and ene reactions with alkenes. Furthermore, the conversions of the representative HDA adduct to nitrone and 2-amino alcohols were demonstrated. Compared with previous metal-catalyzed oxidation methods, this work provides a more efficient and environmentally friendly procedure.

AB - As a first non-metal-catalyzed oxidation for the in situ generation of acylnitroso species, we describe the hypoiodite catalysis using tetra-n-butylammonium iodide as precatalyst with tert-butyl hydroperoxide or hydrogen peroxide as a terminal oxidant. This method can be applied to hetero Diels–Alder (HDA) reactions with dienes and ene reactions with alkenes. Furthermore, the conversions of the representative HDA adduct to nitrone and 2-amino alcohols were demonstrated. Compared with previous metal-catalyzed oxidation methods, this work provides a more efficient and environmentally friendly procedure.

KW - Acylnitroso

KW - Catalysis

KW - Cycloaddition

KW - Ene reaction

KW - Iodine

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JO - European Journal of Organic Chemistry

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ER -

Hetero Diels–Alder Reaction and Ene Reaction of Acylnitroso Species in situ Generated by Hypoiodite Catalysis

Abstract

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