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Mild and efficient nickel-catalyzed Heck reactions with electron-rich olefins.

Artikel i vetenskaplig tidskrift
Författare Thomas M Gøgsig
Jonatan Kleimark
Sten O. Nilsson Lill
Signe Korsager
Anders T Lindhardt
Per-Ola Norrby
Troels Skrydstrup
Publicerad i Journal of the American Chemical Society
Volym 134
Nummer/häfte 1
Sidor 443-52
ISSN 0002-7863
Publiceringsår 2012
Publicerad vid Institutionen för kemi och molekylärbiologi
Sidor 443-52
Språk en
Länkar dx.doi.org/10.1021/ja2084509
Ämneskategorier Kemi

Sammanfattning

A new efficient protocol for the nickel-catalyzed Heck reaction of aryl triflates with vinyl ethers is presented. Mild reaction conditions that equal those of the corresponding palladium-catalyzed Heck reaction are applied, representing a practical and more sustainable alternative to the conventional regioselective arylation of vinyl ethers. A catalytic system comprised of Ni(COD)(2) and 1,1'-bis(diphenylphosphino)ferrocene (DPPF) in combination with the tertiary amine Cy(2)NMe proved effective in the olefination of a wide range of aryl triflates. Both electron-deficient and electron-rich arenes proved compatible, and the corresponding aryl methyl ketone could be secured after hydrolysis in yields approaching quantitative. Good functional group tolerance was observed matching the characteristics of the analogous Pd-catalyzed Heck reaction. The high levels of catalytic activity were explained by the intermediacy of a cationic nickel(II) complex potentially responsible for the successive β-hydride elimination and base promoted catalyst regeneration. Although these elementary reactions are normally considered challenging, DFT calculations suggested this pathway to be favorable under the applied reaction conditions.

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