Fe-Catalyzed Fluoroalkyl(hetero)arylation of Vinyl Azaarenes: Rapid and Modular Synthesis of Unsymmetrical 1,1-Bis(hetero)arylalkanes

Organic Letters, Год журнала: 2024, Номер 26(33), С. 7015 - 7020

Опубликована: Авг. 14, 2024

In contrast to transition-metal-catalyzed difunctionalization of activated alkenes, selective alkylarylation vinyl azaarenes is underdeveloped. Consequently, the lack modular and rapid syntheses 1,1-bis(hetero)arylalkanes limits their exploration in medicinal chemistry. Herein we report a protocol using commercially available iron salts, bisphosphine ligands, fluoroalkyl halides, Grignard reagents that enables 1,2-fluoroalkyl(hetero)arylation azaarenes. We demonstrate versatility robustness method through synthesis range unsymmetrical 1,1-bis(hetero)arylalkenes, including pyridine N-oxides, triazoles, pyrazines, carbazoles, indazoles, 1,2-azaborines. Mechanistic insights from experimental computational investigations support radical pathway provide into role non-covalent interactions catalysis.

Язык: Английский

Intermolecular Regioselective Alkylarylation of Vinylarenes via Photoredox/Nickel Dual Catalysis

Organic Letters, Год журнала: 2024, Номер 26(35), С. 7291 - 7296

Опубликована: Авг. 22, 2024

A novel photoredox/nickel dual catalytic intermolecular alkylarylation of vinylarenes with tertiary and secondary alkyltrifluoroborates aryl bromides is described, which affords 1,1-diarylalkane frameworks that are found in various natural products as well functionalized molecules good to excellent yield regioselectivity through a radical relay process. Notably, this redox-neutral reaction could proceed efficiently tolerance substrates, including great diversity commercially available (hetero)aryl bromides, alkyltrifluoroborates, vinylarenes.

Язык: Английский

Radical Alkylation and Protonation Induced anti-Markovnikov Hydroalkylation of Unactivated Olefins via Cobalt Catalysis

Chemical Communications, Год журнала: 2024, Номер 60(69), С. 9258 - 9261

Опубликована: Янв. 1, 2024

A cobalt catalyzed reductive hydroalkylation of unactivated olefins with anti-Markovnikov selectivity was reported to access complex alkyl amides.

Язык: Английский