Nickel-Catalyzed Inter- and Intramolecular Reductive Cross-Coupling Reactions of Arylbenzylammonium Salts through Highly Site-Selective C–N Bond Cleavage

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5039 - 5046

Published: March 20, 2024

The site selectivity has been investigated for the C–N bond cleavage of arylbenzylammonium salts in reductive cross-coupling reactions with carbon electrophiles. A wide variety triflates participated nickel-catalyzed zinc-mediated benzyl–aryl cross-electrophile coupling aryl bromides to afford diarylmethanes extremely high selectivity. same reaction conditions were successfully extended intramolecular benzyl(bromoaryl)ammonium triflates. Moreover, underwent manganese-mediated benzyl–acyl aromatic carboxylic acids presence di-tert-butyl pyrocarbonate. These employ readily available feedstocks and reagents, exhibit benzylic bonds rather than bonds, tolerate a functional groups.

Language: Английский

Magnesium-Mediated Cross-Electrophile Couplings of Aryl 2-Pyridyl Esters with Aryl Bromides for Ketone Synthesis through In Situ-Formed Arylmagnesium Intermediates

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13661 - 13668

Published: Sept. 9, 2024

Aryl 2-pyridyl esters could efficiently undergo cross-electrophile couplings with aryl bromides the aid of magnesium as a reducing metal in absence transition-metal catalyst, leading to unsymmetrical diaryl ketones modest good yields wide functionality compatibility. In addition, reaction be easily scaled up and applied late-stage modification biologically active molecules. Preliminary mechanistic study showed that coupling presumably proceeds through situ formation arylmagnesium reagents key intermediates.

Language: Английский