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Photoinduced cyclization of  o -alkenylaryl isocyanides with (PhS) 2  in the presence of (PhTe) 2  affords the corresponding bisthiolated indene derivatives in good yields via radical cyclization process by thio radical. The procedure can be applied to the construction of tetracyclic systems by using bis( o -aminophenyl) disulfides in place of (PhS) 2 . In sharp contrast, when  o -alkynylaryl isocyanides are employed as the substrates, novel electrocyclic reactions take place upon photoirradiation or heating at 40~80 °C to generate quinoline 2,4-biradical species, which are trapped with organic diselenides, ditellurides, and molecular iodine to give the corresponding 2,4-diseleno-, ditelluro-, and diiodo-quinoline derivatives, respectively, in good yields. The obtained quinoline derivatives are useful synthetic intermediates; for example, cross-coupling reactions using 2,4-diiodoquinolines lead to the preparation of functionalized quinoline derivatives.

Highly selective introduction of heteroatom groups to isocyanides and its application to electrocyclic reactions