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

• Published in: Advanced synthesis & catalysis Vol. 362; no. 3; pp. 688 - 694
• Main Authors: Liu, Yan, Li, Shi‐Jun, Chen, Xiao‐Lan, Fan, Lu‐Lu, Li, Xiao‐Yun, Zhu, Shan‐Shan, Qu, Ling‐Bo, Yu, Bing
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 06.02.2020; Wiley Subscription Services, Inc
• Subjects: 2-functionalized quinolines; 6-endo-trig radical cyclization; Aromatic compounds; Chemistry; Chemistry, Applied; Chemistry, Organic; Mn(III)-mediated; o-vinylaryl isocyanides; Organic compounds; Physical Sciences; Quinoline; regioselective; Science & Technology; o-vinylaryl isocyanides; PHENANTHRIDINE DERIVATIVES; HETEROAROMATICS QUINOLINES; CATALYZED REACTIONS; SUSTAINABLE SYNTHESIS; 6-endo-trig radical cyclization; regioselective; Mn(III)-mediated; MULTICOMPONENT REACTIONS; MODULAR SYNTHESIS; TANDEM REACTION; 2-functionalized quinolines; OXIDATIVE CYCLIZATION; MICROWAVE-ASSISTED SYNTHESIS; C-H
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201901300

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.