The first study on the reaction of C+-C-Se− 1,3-dipoles with electron-deficient alkenes and alkyne is reported. 2-Arylselenocarbamoylthiazolium inner salts, the unique thiazole carbene-derived C+-C-Se− 1,3-dipoles, reacted efficiently with methoxycarbonylallenes or dimethyl acetylenedicarboxylate to produce dihydroselenophenes or selenopheno[2,3-b]pyrazines, respectively, in high yields. Both reactions probably proceeded via a [3 + 2] cycloaddition of C+-C-Se− 1,3-dipoles with alkenes or alkyne followed by different transformations of the thiazole-spiro-selenophene intermediates. This work provides a concise and efficient strategy for the construction of multifunctional dihydroselenophenes and selenopheno[2,3-b]pyrazines, which are not easy accessible by other methods.
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