Electrochemical N‐Centered Radical Addition/Semipinacol Rearrangement Sequence of Alkenyl Cyclobutanols: Synthesis of β‐Amino Cyclic Ketones

The electrochemical N‐centered radical addition/semipinacol rearrangement sequence of alkenyl cyclobutanols with sulfonimides is described. This transformation is an environmentally friendly approach that uses cheap and easily handled sulfonimides as N‐centered radical sources and successfully avoid...

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Veröffentlicht in:Asian journal of organic chemistry 2022-12, Vol.11 (12), p.n/a
Hauptverfasser: Jang, Jihoon, Kim, Dae Young
Format: Artikel
Sprache:eng
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Zusammenfassung:The electrochemical N‐centered radical addition/semipinacol rearrangement sequence of alkenyl cyclobutanols with sulfonimides is described. This transformation is an environmentally friendly approach that uses cheap and easily handled sulfonimides as N‐centered radical sources and successfully avoiding the use of stoichiometric amounts of external redox reagents. The β‐amino cyclic ketone derivatives could be synthesized in moderate to high yields from alkenyl cyclobutanol derivatives under mild constant current electrolysis conditions. The electrochemical N‐centered radical addition/semipinacol rearrangement sequence was successfully achieved of alkenyl cyclobutanols with sulfonimides. This approach was environmentally benign by avoiding the use of stoichiometric amounts of external redox reagents. The β‐amino cyclic ketone derivatives were obtained from alkenyl cyclobutanol derivatives in moderate to high yields under mild constant current electrolysis conditions.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.202200531