Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition
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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; Park, Cheol-Min
- Issue Date
- AMER CHEMICAL SOC
- ORGANIC LETTERS, v.22, no.14, pp.5528 - 5534
- 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.
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