Photoinduced, copper-catalyzed three-component radical annulation of gem -dialkylthio enynes, cyclobutanone oxime esters, and boronic acids was achieved, forming highly functionalized aryl thienyl sulfides with both good chemo- and diastereoselectivities. The reaction proceeds through a domino sequence involving cyanoalkyl radical-mediated intramolecular annulation of gem -dialkylthio enyne, alkenyl radical-promoted C(sp 3 )–S bond cleavage, and sulfur-centered radical-trapped Cu(II)-facilitated C–S cross-coupling. The protocol features simultaneous establishment of cyanoalkyl, cyclopentanone, and thiophene moieties and a thioether C–S bond in one pot with broad substrate scopes and versatile functional group tolerance under mild conditions.
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Lou et al. (2020) studied this question.