Rh(I)-Catalyzed Carbon–Carbon Double-Bond Formation by Coupling of (Quinolin-8-yl)methanone with Arylaldehyde Tosylhydrazone

Abstract

An alternative method for the direct arylvinylation of (quinolin-8-yl)methanone with substituted N′-benzylidene-4-methyl­benzenesulfonohydrazide is described. The desired 3-aryl-1-(quinolin-8-yl)prop-2-en-1-one products are obtained in high yields through the catalytic reaction of (quinolin-8-yl)methanone and N′-arylidene-4-methylbenzenesulfonohydrazide (2 equiv) with [Rh(PPh₃)₃Cl] (10 mol%), Ag₂O (0.5 equiv), and Cs₂CO₃ (2 equiv) at 130 °C for 48 hours. Two plausible mechanisms involving C–H activation and migratory insertion of the carbene into the rhodium–carbon bond were proposed to explain the formation of the product.

Key words

quinolinone - rhodium complex - hydrazones - C–C ­coupling - double-bond formation

• References and Notes


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• 15 Synthesis of 3-Phenyl-1-(quinolin-8-yl)prop-2-en-1-one (Scheme 2 and Table 3, Entry 1); Typical Procedure: A mixture of (quinolin-8-yl)methanone (85.5 mg, 0.5 mmol), N′-benzylidene-4-methylbenzenesulfonohydrazide (548.6 mg, 1.0 mmol), Ag₂O (58.0 mg, 0.25 mmol), Cs₂CO₃ (232 mg, 1.0 mmol), and [Rh(PPh₃)₃Cl] (46.65 mg, 0.05 mmol) under nitrogen in a screw-capped thick-walled Pyrex tube was heated at 130 °C with stirring. After heating for 48 h, the reaction mixture was cooled and directly purified by column chromatography on silica gel (hexane–EtOAc, 20:1) to afford 3-phenyl-1-(quinolin-8-yl)prop-2-en-1-one (75% yield).