Electrochemical Radical Selenylation/1,2-Carbon Migration and Dowd Beckwith-Type Ring-Expansion Sequences of Alkenylcyclobutanols

Citations

WEB OF SCIENCE

104
Citations

SCOPUS

105

초록

Electrochemical oxidative radical selenylation/ 1,2 -carbon migration and Dowd-Beckwith-type ring-expansion sequences of alkenylcyclobutanols were developed in this study. This approach is environmentally benign and uses shelf-stable diselenides as selenium radical precursors and electrons as oxidizing reagents. The present protocol offers a facile way to prepare beta-selenated cyclic ketone derivatives. Under Dowd-Beckwith-type rearrangement, it can afford the corresponding one-carbon ring-expanded ketones.

키워드

Electrochemistry; Radical Selenylation/1; 2-Carbon Migration; Dowd−Beckwith-Type Ring-Expansion; Alkenylcyclobutanols; VISIBLE-LIGHT PHOTOREDOX; ASYMMETRIC-SYNTHESIS; H FUNCTIONALIZATION; ARYLBORONIC ACIDS; ARYL MIGRATION; BOND FORMATION; C-SE; REARRANGEMENT; SOLVENT; ALKENES
제목
Electrochemical Radical Selenylation/1,2-Carbon Migration and Dowd Beckwith-Type Ring-Expansion Sequences of Alkenylcyclobutanols
저자
Kim, Yeon Joo; Kim, Dae Young
DOI
10.1021/acs.orglett.8b04041
발행일
2019-02-15
유형
Article
저널명
Organic Letters
권
21
호
4
페이지
1021 ~ 1025