Palladium-Catalyzed Oxidative Direct C3- and C7-Alkenylations of Indazoles: Application to the Synthesis of Gamendazole.

The first palladium-catalyzed oxidative alkenylation of (1H)- and (2H)-indazole derivatives with various olefins is described. The use of Pd(OAc)2 as the catalyst and Ag2CO3 as the oxidant promoted the selective C3-monoalkenylation of (1H)-indazoles and (2H)-indazoles, affording the desired products in good yields. An original oxidative C7-alkenylation of 3-substituted (1H)-indazoles was also developed. The oxidative alkenylation of (1H)-indazole was successfully applied to the total synthesis of the drug candidate gamendazole in a step- and atom-economical fashion.

Citation

Mohammed Naas, Saïd El Kazzouli, El Mokhtar Essassi, Mosto Bousmina, Gérald Guillaumet. Palladium-Catalyzed Oxidative Direct C3- and C7-Alkenylations of Indazoles: Application to the Synthesis of Gamendazole. Organic letters. 2015 Sep 4;17(17):4320-3

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PMID: 26308587

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