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Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition
- Choi, Subin;
- Oh, Hyeonji;
- Sim, Jeongwoo;
- Yu, Eunsoo;
- Shin, Seunghoon;
- 외 1명
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17초록
The synthesis of versatile scaffold indolopyrans based on C-C radical-radical cross-coupling under metal-free conditions is described. The reaction involving single electron transfer between coupling partners followed by cage collapse allows highly selective cross-coupling while employing only equimolar amounts of coupling partners. Moreover, the mechanistic manifold was expanded for the functionalization of enamines to give the stereoselective synthesis of 2,3-dihydrofurans. This iodine-mediated oxidative coupling features mild conditions and fast reaction kinetics.
키워드
PICTET-SPENGLER REACTIONS; SP(3) C-H; INDOLE SYNTHESIS; IODINE(III) REAGENTS; AMINATION; EFFICIENT; FUNCTIONALIZATION; BONDS; TETRAHYDROISOQUINOLINES; ALKYLATION
- 제목
- Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition
- 저자
- Choi, Subin; Oh, Hyeonji; Sim, Jeongwoo; Yu, Eunsoo; Shin, Seunghoon; Park, Cheol-Min
- 발행일
- 2020-07
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 22
- 호
- 14
- 페이지
- 5528 ~ 5534