| Autor: |
Raje S; Schulich Faculty of Chemistry, Technion─Israel Institute of Technology, Technion City, 3200008 Haifa, Israel., Sheikh Mohammad T; Schulich Faculty of Chemistry, Technion─Israel Institute of Technology, Technion City, 3200008 Haifa, Israel., de Ruiter G; Schulich Faculty of Chemistry, Technion─Israel Institute of Technology, Technion City, 3200008 Haifa, Israel. |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2024 Apr 05; Vol. 89 (7), pp. 4319-4325. Date of Electronic Publication: 2024 Mar 23. |
| DOI: |
10.1021/acs.joc.3c02349 |
| Abstrakt: |
Earth-abundant-metal catalyzed double bond transposition offers a sustainable and atom-economical route toward the synthesis of internal alkenes. With an emphasis specifically on internal olefins and ethers, the isomerization of allylic amines has been particularly under represented in the literature. Herein, we report an efficient methodology for the selective isomerization of N -allylic organic compounds, including amines, amides, and imines. The reaction is catalyzed by a neutral PC NHC P cobalt(I) pincer complex and proceeds via a π-allyl mechanism. The isomerization occurs readily at 80-90 °C, and it is compatible with a wide variety of functional groups. The in situ formed enamines could additionally be used for a one-pot inverse-electron-demand Diels-Alder reaction to furnish a series of diversely substituted heterobiaryls, which is further discussed in this report. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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