Open AccessSuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride
Author(s) -
Pavel M. Yamanushkin,
Kemal Kaya,
Mark Aldren Maniquiz Feliciano,
Brian Gold
Publication year - 2022
Publication title -
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 , chemistry , pharmacophore , nucleophile , fluoride , cycloaddition , combinatorial chemistry , catalysis , organic chemistry , computational chemistry , stereochemistry , 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.