Synthesis of chalcogen-functionalized 4H-chromen-4-ones via cyclization/chalcogenation of alkynyl aryl ketones mediated by Selectfluor®

The synthesis of organochalcogen-functionalized chromenones starting from diorganyl dichalcogenides and alkynyl aryl ketones has been developed. Selectfluor (R) mediates these cyclization/organochalcogenation reaction sequences under mild and open-to-air conditions. The six-membered heterocycles were obtained via a selective 6-endo-dig cyclization compatible with the use of both diorganyl diselenides and disulfides. This synthetic methodology still proved to be versatile to synthesize organochalcogen-substituted thiochromenone and isocromenone derivatives.

Automated summary

A synthetic method for organochalcogen-functionalized chromenones has been developed using diorganyl dichalcogenides and alkynyl aryl ketones. Selectfluor(R) mediates the cyclization/organochalcogenation reactions under mild and open-to-air conditions. The versatile methodology allows for the synthesis of organochalcogen-substituted thiochromenone and isocromenone derivatives.