Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF₃-Imidoyl Sulfoxonium Ylides via Triple C–H Activation

Organic Letters, Год журнала: 2025, Номер 27(2), С. 657 - 662

Опубликована: Янв. 7, 2025

A condition-controlled Rh(III)-catalyzed selective synthesis of CF3-substituted indoles and pyrido[2,1-a]isoindoles from 2-arylpyridines CF3-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)3(SbF6)2/HFIP system afforded via triple C–H activation, while the [Cp*RhCl2]2/MeCN condition selectively furnished through [4 + 1] annulation. notable advantages this developed method included readily available starting materials, broad substrate scope, excellent chemoselectivity. Importantly, several selected products showed promising antitumor activities.

Язык: Английский

In Situ Generation and [3 + 2] Annulation Reactions of Propiolaldehyde─A Metal-Free, Cascade Route to Pyrazole and Bipyrazole Carboxaldehydes in One Pot

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Май 7, 2025

Propiolaldehyde, the most reactive yet less explored electrophilic acetylene, was generated in situ via a base-free Kornblum oxidation from propargyl tosylate and successfully intercepted with hydrazones affording pyrazole-4-carboxaldehyde one-pot by [3 + 2] annulation reaction. Further, endured unique cascade reaction phenylhydrazine tosylate, yielding synthetically challenging bipyrazole carboxaldehydes. The method is free of any metal catalyst, base, or additives offers convenient protocol to handle volatile propiolaldehyde under ambient conditions.

Язык: Английский