Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition

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13
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17

초록

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
DOI
10.1021/acs.orglett.0c01896
발행일
2020-07
유형
Article
저널명
Organic Letters
권
22
호
14
페이지
5528 ~ 5534