JOURNAL ARTICLE

Enantioselective Synthesis of Functionalized Arenes by Nickel‐Catalyzed Site‐Selective Hydroarylation of 1,3‐Dienes with Aryl Boronates

Justin S. MarcumTiffany R. TaylorSimon J. Meek

Year: 2020 Journal:   Angewandte Chemie International Edition Vol: 59 (33)Pages: 14070-14075   Publisher: Wiley

Abstract

Abstract A catalytic method for the site‐selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3‐dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol % of a readily available monodentate phosphoramidite‐Ni complex in ethanol, affording a variety of enantioenriched products in up to 96 % yield and 99:1 er. Mechanistic studies indicate that Ni–allyl formation is irreversible and related to the nature of the arylboronate.

Keywords:
Enantioselective synthesis Aryl Catalysis Nickel Chemistry Combinatorial chemistry Organic chemistry

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Topics

Catalytic C–H Functionalization Methods
Physical Sciences →  Chemistry →  Organic Chemistry
Asymmetric Hydrogenation and Catalysis
Physical Sciences →  Chemistry →  Inorganic Chemistry
Catalytic Cross-Coupling Reactions
Physical Sciences →  Chemistry →  Organic Chemistry
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