SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride | Zendy

Pavel Yamanushkin | Zendy; Kemal Kaya | Zendy; Mark Aldren M. Feliciano | Zendy; Brian Gold | Zendy

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SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride

Author(s) -

Pavel Yamanushkin,

Kemal Kaya,

Mark Aldren M. Feliciano,

Brian Gold

Publication year - 2022

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.1c03105

Subject(s) - diazo , fluoride , chemistry , organic chemistry , combinatorial chemistry , inorganic chemistry

"Click" reactions have transformed the molecular sciences. Augmenting cycloaddition reactions, sulfur(VI) fluoride exchange (SuFEx) chemistry has diversified the landscape of molecular assembly. Herein, we report a facile strategy to access SuFExable NH -pyrazoles via strain and catalyst-free 1,3-dipolar cycloadditions of stabilized diazo compounds under mild conditions. Subsequent SuFEx proceeds efficiently with various N - and O -nucleophiles. Access to SuFExable NH -pyrazoles─a class of compounds containing two common pharmacophores─enables future opportunities within drug discovery, chemical biology, materials chemistry, and related fields.

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