Clickable Transformation of Nitriles (RCN) to Oxazolyl Sulfonyl Fluoride Warheads

The protocol for simple, efficient, and mild synthesis of oxazolyl sulfonyl fluorides was developed through Rh2(OAc)4-catalyzed annulation of methyl-2-diazo-2-(fluorosulfonyl)­acetate (MDF) or its ethyl ester derivative with nitriles. This practical method provides a general and direct route to a un...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 22; pp. 8904 - 8909
Main Authors Fang, Wan-Yin, Wang, Shi-Meng, Zhang, Zai-Wei, Qin, Hua-Li
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.11.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DEOXYFLUORINATION
FUNCTIONALIZED OXAZOLES
2,5-DISUBSTITUTED OXAZOLES
INHIBITORS
EFFICIENT
CATALYZED-REACTIONS
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Summary:The protocol for simple, efficient, and mild synthesis of oxazolyl sulfonyl fluorides was developed through Rh2(OAc)4-catalyzed annulation of methyl-2-diazo-2-(fluorosulfonyl)­acetate (MDF) or its ethyl ester derivative with nitriles. This practical method provides a general and direct route to a unique class of highly functionalized oxazolyl-decorated sulfonyl fluoride warheads with great potential in medicinal chemistry, chemical biology, and drug discovery.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03298