Assembly of Thiosubstituted Benzoxazoles via Copper-Catalyzed Coupling of Thiols with 5-Iodotriazoles Serving as Diazo Surrogates

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An efficient cascade approach to thiosubstituted benzoxazoles has been developed. The transformation starts with in situ generation of a diazo compound via annulation-triggered electrocyclic opening of the 1,2,3-triazole ring. The subsequent Cu-catalyzed trapping of diazo intermediates by various thiols affords the desired heterocycles in generally good yields of up to 91%. The protocol features very good functional group tolerance and is applicable to substrates with different electronic properties.
Publisher
American Chemical Society
Issue Date
2020-07
Language
English
Article Type
Article
Citation

Journal of Organic Chemistry, v.85, no.14, pp.9015 - 9028

ISSN
0022-3263
DOI
10.1021/acs.joc.0c00931
URI
http://hdl.handle.net/10203/281226
Appears in Collection
PH-Journal Papers(저널논문)
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