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镍催化乙烯基芳烃的α-羰基烷基芳基化反应:γ,γ-二芳基羰基和芳基四氢萘酮衍生物的便捷合成方法。

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

机构信息

Department of Chemistry and Chemical Biology, University of New Mexico, 300 Terrace St. NE, Albuquerque, NM, USA.

Department of Chemistry, Pennsylvania State University, University Park, PA, 16802, USA.

出版信息

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

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.

摘要

我们报告了一种镍催化的乙烯基芳烃与α-卤代羰基化合物和芳基锌试剂的区域选择性α-羰基烷基芳基化反应。该反应适用于伯、仲和叔α-卤代羰基分子以及电子变化的芳基锌试剂。该反应生成具有α-仲、叔和季碳原子的γ,γ-二芳基羰基衍生物。产物可以很容易地转化为芳基四氢萘酮,包括抗抑郁药百忧解的前体。

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