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

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초록

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 beta-amino cyclic ketone derivatives could be synthesized in moderate to high yields from alkenyl cyclobutanol derivatives under mild constant current electrolysis conditions.

키워드

Amination; alkenyl cyclobutanols; beta-amino ketones; electrosynthesis; VISIBLE-LIGHT PHOTOREDOX; C-H FUNCTIONALIZATION; MIGRATION SEQUENCES; RING EXPANSION; SEMIPINACOL REARRANGEMENTS; ELECTROCATALYTIC APPROACH; ASYMMETRIC-SYNTHESIS; MANNICH-BASES; QUINOXALIN-2(1H)-ONES; DIFUNCTIONALIZATION
제목
Electrochemical N-Centered Radical Addition/Semipinacol Rearrangement Sequence of Alkenyl Cyclobutanols: Synthesis of beta-Amino Cyclic Ketones
저자
Jang, Jihoon; Kim, Dae Young
DOI
10.1002/ajoc.202200531
발행일
2022-12
유형
Article
저널명
Asian Journal of Organic Chemistry
권
11
호
12