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Ruthenium-catalyzed room-temperature coupling of α-keto sulfoxonium ylides and cyclopropanols for δ-diketone synthesis.

Previous transition metal-catalyzed synthesis processes of δ-diketones are plagued by the high cost of the rhodium catalyst and harsh reaction conditions. Herein a low-cost, room temperature ruthenium catalytic method is… Click to show full abstract

Previous transition metal-catalyzed synthesis processes of δ-diketones are plagued by the high cost of the rhodium catalyst and harsh reaction conditions. Herein a low-cost, room temperature ruthenium catalytic method is developed based on the coupling of α-keto sulfoxonium ylides with cyclopropanols. The mild protocol features a broad substrate scope (47 examples) and a high product yield (up to 99%). Mechanistic studies argue against a radical pathway and support a cyclopropanol ring opening, sulfoxonium ylide-derived carbenoid formation, migratory insertion C-C bond formation pathway.

Keywords: room temperature; sulfoxonium ylides; sulfoxonium; keto sulfoxonium; coupling keto; ylides cyclopropanols

Journal Title: Chemical communications
Year Published: 2021

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