Electrochemical radical arylsulfonylation/semipinacol rearrangement sequences of alkenylcyclobutanols: Synthesis of beta-sulfonated cyclic ketones

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초록

Electrochemical oxidative radical sulfonylation/semipinacol rearrangement sequences of alkenylcyclobutanols have been developed. The reaction proceeds in an undivided electrochemical cell equipped with platinum plate electrodes employing sodium iodide as a redox catalyst and a supporting electrolyte. This approach is environmentally benign by using shelf-stable arylsulfonyl hydrazides as arylsulfonyl radical precursor and electrons as oxidizing reagents. The present protocol offers a facile way to prepare beta-sulfonated cyclic ketone derivatives. (C) 2019 Elsevier Ltd. All rights reserved.

키워드

Sulfonylation; Electrochemical oxidation; Semipinacol rearrangement; Alkenyl alcohols; VISIBLE-LIGHT PHOTOREDOX; METAL-FREE SYNTHESIS; MIGRATION SEQUENCES; AEROBIC DIFUNCTIONALIZATION; SEMIPINACOL REARRANGEMENT; TERMINAL ALKYNES; CINNAMIC-ACIDS; SULFUR-DIOXIDE; RING EXPANSION; SULFONYLATION
제목
Electrochemical radical arylsulfonylation/semipinacol rearrangement sequences of alkenylcyclobutanols: Synthesis of beta-sulfonated cyclic ketones
저자
Kim, Yeon Joo; Kim, Dae Young
DOI
10.1016/j.tetlet.2019.04.009
발행일
2019-05-02
유형
Article
저널명
Tetrahedron Letters
권
60
호
18
페이지
1287 ~ 1290