Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium

Moon, Sanghun; Nishii, Yuji; Miura, Masahiro

Organic Letters, 2021, 23(1), 49-53

Number of Access:293（2025-11-05 02:43 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/92812

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Title
Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium
Creator
CreatorName
Moon, Sanghun
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
1000020183626 1000020183626
ORCID
0000-0001-8288-6439 0000-0001-8288-6439
researchmap permalink
read0013936 read0013936
Scopus Author ID
7402799909 7402799909
CreatorName
Miura, Masahiro
Description
Moon S., Nishii Y., Miura M.. Synthesis of Isothiazoles and Isoselenazoles through Rhodium-Catalyzed Oxidative Annulation with Elemental Sulfur and Selenium. Organic Letters. 23(1), 49-53, (2021), 1 January 2021; ©2021 American Chemical Society. https://doi.org/10.1021/acs.orglett.0c03674.
Abstract
A rhodium-catalyzed oxidative annulation of benzimidates with elemental sulfur for the direct construction of isothi-azole rings is reported. The proposed reaction mechanism involving Rh(I)/Rh(III) redox is supported by a stoichiometric reaction of metallacycle species as well as DFT calculations. This method is also applicable to the selenium cyclization to produce isoselenazole derivatives. The alkoxy substituent at the C3 position can be used for further functionalization of the azole cores.
Publisher
American Chemical Society
Source Title
Organic Letters
Volume (Issue)
23(1)
Page
49-53
Date of Issued
2021-01-01
Language
English
Handle URL
https://hdl.handle.net/11094/92812
PISSN
15237060
eISSN
15237052
NCID
AA11347843
Relation.isVersionOf
DOI (Publisher Version)
https://doi.org/10.1021/acs.orglett.0c03674
Access Rights
open access
CopyRight
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.0c03674.
oaire:version
Accepted Manuscript
Category
学術雑誌論文 Journal Article