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ID 55328
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Author
Iwasaki, Masayuki Research Institute for Interdisciplinary Science, Okayama University
Miki, Natsumi Graduate School of Natural Science and Technology, Okayama University
Tsuchiya, Yuta Graduate School of Natural Science and Technology, Okayama University
Nakajima, Kiyohiko Department of Chemistry, Aichi University of Education
Nishihara, Yasushi Research Institute for Interdisciplinary Science, Okayama University
Abstract
Nickel-catalyzed direct selenation of benzamides bearing an 8-quinolyl auxiliary with elemental selenium provides benzoisoselenazolones in good yield via carbon-selenium and nitrogen-selenium bond formation under aerobic conditions. In addition to aryl C-H bonds, the method can also be applied to alkenyl C-H bonds, constructing an isoselenazolone skeleton. Simple mechanistic analysis shows that the reaction proceeds through a rate-determining C-H bond cleavage. The obtained benzoisoselenazolones are transformed into various organoselenium compounds and utilized as the catalyst for bromolactonization of alkenoic acids.
Note
This is an Accepted Manuscript of an article published by American Chemical Society
Published Date
2017-02-17
Publication Title
Organic Letters
Volume
volume19
Issue
issue5
Publisher
American Chemical Society
Start Page
1092
End Page
1095
ISSN
1523-7060
NCID
AA11347843
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
Copyright Holders
https://creativecommons.org/licenses/by-nc-nd/4.0/deed.ja
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DOI
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Related Url
https://doi.org/10.1021/acs.orglett.7b00116