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. 2020 May 18;59(21):8047-8051.
doi: 10.1002/anie.201913435. Epub 2020 Mar 19.

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives

Shekhar Kc  1 , Roshan K Dhungana  2 , Namrata Khanal  1 , Ramesh Giri  2
Affiliations

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives

Shekhar Kc et al. Angew Chem Int Ed Engl. .

Abstract

We report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-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.

Keywords: aryltetralones; diarylcarbonyl compounds; dicarbofunctionalization; nickel catalysis; vinylarenes.

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Figures

Scheme 1.
Scheme 1.
Bioactive and Naturally Occurring γ,γ-Diaryl Esters and Aryltetralone Cores
Scheme 2.
Scheme 2.
Synthesis of aryltetralone derivatives
Scheme 3.
Scheme 3.
Reaction with TEMPO
Scheme 4.
Scheme 4.
Radical clock experiment
Scheme 5:
Scheme 5:
Proposed catalytic cycle
See this image and copyright information in PMC

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