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

被引：10

作者：

Choi, Subin ^{[1
]}

Oh, Hyeonji ^{[1
]}

Sim, Jeongwoo ^{[1
]}

Yu, Eunsoo ^{[1
]}

Shin, Seunghoon ^{[2
]}

Park, Cheol-Min ^{[1
]}

机构：

[1] UNIST Ulsan Natl Inst Sci & Technol, Dept Chem, Ulsan 44919, South Korea

[2] Hanyang Univ, Dept Chem, Seoul 04763, South Korea

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 14期

基金：

新加坡国家研究基金会;

关键词：

PICTET-SPENGLER REACTIONS; SP(3) C-H; INDOLE SYNTHESIS; IODINE(III) REAGENTS; AMINATION; EFFICIENT; FUNCTIONALIZATION; BONDS; TETRAHYDROISOQUINOLINES; ALKYLATION;

D O I：

10.1021/acs.orglett.0c01896

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：5528 / 5534

页数：7

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