Metal-Free Synthesis of Indolopyrans and 2,3-Dihydrofurans Based on Tandem Oxidative Cycloaddition
- Authors
- Choi, Subin; Oh, Hyeonji; Sim, Jeongwoo; Yu, Eunsoo; Shin, Seunghoon; Park, Cheol-Min
- Issue Date
- Jul-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.22, no.14, pp.5528 - 5534
- Indexed
- SCIE
SCOPUS
- Journal Title
- ORGANIC LETTERS
- Volume
- 22
- Number
- 14
- Start Page
- 5528
- End Page
- 5534
- URI
- https://scholarworks.bwise.kr/hanyang/handle/2021.sw.hanyang/145450
- DOI
- 10.1021/acs.orglett.0c01896
- ISSN
- 1523-7060
- Abstract
- 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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