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

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 Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2020, Volume: 362, Number: 18, Pages: 3864-3871 Pages count : 8 DOI: 10.1002/adsc.202000618

Authors

Paveliev Stanislav A. ¹ , Churakov Artem I. ¹ , Alimkhanova Liliya S. ¹ , Segida Oleg O. ¹ , Nikishin Gennady I. ¹ , Terent'ev Alexander O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., Moscow, 119991 Russian Federation

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%.

Paveliev S.A. , Churakov A.I. , Alimkhanova L.S. , Segida O.O. , Nikishin G.I. , Terent'ev A.O.
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
Advanced Synthesis & Catalysis. 2020. V.362. N18. P.3864-3871. DOI: 10.1002/adsc.202000618 WOS Scopus OpenAlex

Web of science:	WOS:000552741900001
Scopus:	2-s2.0-85088582587
OpenAlex:	W3042337814

DB	Citing
OpenAlex	25
Scopus	23
Web of science	23