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We report a catalytic strategy that generates rhodium-carbynoids by selective diazo activation of designed carbyne sources. We found that rhodium-carbynoid species provoke C( sp  2 )-C( sp  2 ) bond scission in alkenes by inserting a monovalent carbon unit between both sp  2 -hybridized carbons. This skeletal remodeling process accesses synthetically useful allyl cation intermediates that conduct to valuable allylic building blocks upon nucleophile attack. Our results rely on the formation of cyclopropyl-I (III) intermediates able to undergo electrocyclic ring-opening, following the Woodward-Hoffmann-DePuy rules.

Catalytic Cleavage of C(sp2)–C(sp2) Bonds with Rh-Carbynoids

Catalytic Cleavage of C(sp²)–C(sp²) Bonds with Rh-Carbynoids