Additive-Free Radical Cascade Reaction of Oxime Esters: Synthesis of Pyrroline-Functionalized Phenanthridines

A variety of dihydropyrrole-functionalized phenanthridines were efficiently synthesized by the metal-free, radical cascade cyclization reaction of 2-isocyanobiphenyls with γ,δ-unsaturated oxime esters. The C–N/C–C/C–C bonds were formed via the oil bath method in a one-pot procedure with broad substr...

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Veröffentlicht in:Journal of organic chemistry 2020-10, Vol.85 (19), p.12284-12293
Hauptverfasser: Xue, Yijie, Xue, Dengqi, He, Qian, Ge, Qianwei, Li, Wei, Shao, Liming
Format: Artikel
Sprache:eng
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Zusammenfassung:A variety of dihydropyrrole-functionalized phenanthridines were efficiently synthesized by the metal-free, radical cascade cyclization reaction of 2-isocyanobiphenyls with γ,δ-unsaturated oxime esters. The C–N/C–C/C–C bonds were formed via the oil bath method in a one-pot procedure with broad substrate applicability. The radical process was supported by kinetic isotope effect studies and radical inhibition studies.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.0c01532