4.7 Article

Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 362, Issue 3, Pages 688-694

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201901300

Keywords

Mn(III)-mediated; regioselective; 6-endo-trig radical cyclization; 2-functionalized quinolines; o-vinylaryl isocyanides

Funding

  1. National Natural Science Foundation of China [21501010, 21971224]
  2. China Postdoctoral Science Foundation [2019M652561]
  3. Key Research Projects of Universities in Henan Province [20A150006, 20B150021]
  4. Henan Province Young Talents Elevation Program [2019HYTP023]
  5. Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation [2019CL03]

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A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.

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