The Rh(III)‐catalyzed ortho‐C−H bond functionalization of 2‐aryl indazoles with β‐ketosulfoxonium ylides has been developed for the synthesis of 6‐arylindazolo[2,3‐a]quinoline derivatives in good to excellent yields with a broad substrate scope and good functional group tolerance. The reaction proceeds through a sequential ortho‐alkylation followed by cyclodehydration. The combination of 5 mol% of Cp*Rh(III) and 40 mol% AgSbF6 was found to be effective for this conversion.
An Ir(III)-catalyzed double C−H activation strategy has been developed for the synthesis of highly rigid spiro frameworks by means of ortho-functionalization of 2-aryl phthalazinediones and 2,3-diphenylcycloprop-2-en-1-ones using the Ir(III)/AgSbF 6 catalytic system. Similarly, 3-aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides undergo smooth cyclization with 2,3diphenylcycloprop-2-en-1-ones to afford a diverse range of spiro compounds in good yields with excellent selectivity. Additionally, 2arylindazoles provide the corresponding chalcone derivatives under similar reaction conditions.
Rh(III)-catalyzed CÀ H bond annulation of 2-arylquinoxalines with cyclic 2-diazo-1,3-diketones has been accomplished for the first time to synthesize a novel series of 2,3dihydrodibenzo[a,c]phenazin-4(1H)-one frameworks by means of carbene insertion followed by condensation. The reaction proceeds through the CÀ H bond activation and functionalization of 2-arylquinoxalines using Rh(III)/AgSbF 6 complex to produce highly substituted 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-one and benzo [5,6][1,2,4]thiadiazino[2,3-f]phenanthridin-5(6H)-one-10,10-dioxide derivatives in good to excellent yields.
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