Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Xu-Xu, Qing Feng; Nishii, Yuji; Uetake, Yuta et al.

Chemistry - A European Journal, 2021, 27(71), 17952-17959

Number of Access:618（2025-12-22 03:21 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92779

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Title
Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium
Creator
CreatorName
Xu-Xu, Qing Feng
NRID
1000070773787 1000070773787
ORCID
0000-0002-6824-0639 0000-0002-6824-0639
researchmap permalink
y_nishii y_nishii
Scopus Author ID
55233363700 55233363700
CreatorName
Nishii, Yuji
NRID
1000010755440 1000010755440
ORCID
0000-0002-4742-8085 0000-0002-4742-8085
researchmap permalink
yutauetake yutauetake
Scopus Author ID
56417952700 56417952700
CreatorName
Uetake, Yuta
NRID
1000000262147 1000000262147
ORCID
0000-0001-5783-4151 0000-0001-5783-4151
researchmap permalink
read0184917 read0184917
Scopus Author ID
7402869823 7402869823
CreatorName
Sakurai, Hidehiro
NRID
1000020183626 1000020183626
ORCID
0000-0001-8288-6439 0000-0001-8288-6439
researchmap permalink
read0013936 read0013936
Scopus Author ID
7402799909 7402799909
CreatorName
Miura, Masahiro
Subject
annulation
benzoisoselenazolone
C−H functionalization
rhodium catalysis
selenium
Description
This is the accepted version of the following article: Xu-Xu Q.F., Nishii Y., Uetake Y., et al. Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium. Chemistry - A European Journal 27, 17952 (2021); which has been published in final form at https://doi.org/10.1002/chem.202103485. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html]
Abstract
Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.
Publisher
John Wiley and Sons Inc
Source Title
Chemistry - A European Journal
Volume (Issue)
27(71)
Page
17952-17959
Date of Issued
2021-12-20
Language
English
Handle URL
https://hdl.handle.net/11094/92779
PISSN
09476539
eISSN
15213765
NCID
AA11076269
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1002/chem.202103485
Access Rights
open access
CopyRight
© 2021 Wiley-VCH GmbH
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article