Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ, γ-Diarylcarbonyl and Aryltetralone Derivatives
Shekhar KC, Roshan Dhungana, Namrata Khanal, and Ramesh Giri*—Angew. Chem. Int. Ed. 2020, 59, 8047–8051/10.1002/anie.201913435
Recommended by Zhe Cui
KEY WORDS: Aryltetralones, Diarylcarbonyl compounds, Dicarbofunctionalization, Nickel catalysis, Vinylarenes
ABSTRACT: The authors report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with γ, γ-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary and tertiary α-halocarbonyl molecules, and electronically varied arylzinc reagents. The reaction generates γ, γ-diarylcarbonyl derivatives with α-secondary, tertiary and quaternary carbon centers. The products can be readily converted to aryltetralones, including a precursor to Zoloft, an antidepressant drug.
Optimization of reaction conditions.
Scope with ArZnI.
Scope with vinylarenes, RX and ArZnI.
Proposed Mechanism.
One-pot, two-step synthesis of aryl tetralones.
Summary and Comments:
A multicomponent nickel-catalyzed 1,2-difunctionalization of vinylarenes is reported. By employing a one-pot, two-step strategy, aryl tetralones were generated by the reported Ni-catalyzed methodology, followed by an intramolecular Friedel–Crafts acylation. The above radical-type mechanism was supported by a TEMPO trapping experiment.