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Electrochemical Synthesis of O ‐Phthalimide Oximes from α ‐Azido Styrenes via Radical Sequence: Generation, Addition and Recombination of Imide‐ N ‐Oxyl and Iminyl Radicals with C−O/N−O Bonds Formation
Author(s) -
Paveliev Stanislav A.,
Churakov Artem I.,
Alimkhanova Liliya S.,
Segida Oleg O.,
Nikishin Gennady I.,
Terent'ev Alexander O.
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000618
Subject(s) - phthalimide , chemistry , imide , radical , radical cyclization , electrochemistry , polymer chemistry , free radical reaction , photochemistry , medicinal chemistry , organic chemistry , electrode
Electrochemically induced radical‐initiated reaction of vinyl azides with N ‐hydroxyphthalimide resulting O ‐phthalimide oximes with challenging for organic chemistry N−O‐N fragment has been discovered. The developed approach introduces in synthesis electrochemically generated O‐centered imide‐ N ‐oxyl radicals as the coupling components. Sequential formation of C−O and N−O bonds was achieved via generation and selective addition of imide‐ N ‐oxyl radicals, followed by recombination with iminyl radicals. A wide range of O ‐phthalimide oximes was obtained with the yields up to 84%.