| Autor: |
Fichez, Jeanne, Lapuh, Maria I., Truong, Lina, Oulyadi, Hassan, Buttard, Floris, Besset, Tatiana |
| Předmět: |
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| Zdroj: |
Advanced Synthesis & Catalysis; 6/18/2024, Vol. 366 Issue 12, p2811-2822, 12p |
| Abstrakt: |
A palladium(II)‐catalyzed oxidative C−H olefination of chlorobenzene derivatives, which favored the functionalization at the ortho‐to‐chlorine position, was reported. The catalytic system employed a commercially available quinoline ligand to access a wide panel of olefinated aryl chlorides in moderate to high yields from feedstock chemicals (42 examples, 28 to 93% yields). The synthetic utility of the method was further demonstrated by the coupling of various bio‐relevant acrylate partners offering straightforward access to structurally diverse complex molecules. A computational study of the reaction allowed us to confirm that the C−H activation step, occurring through a Concerted Metalation‐Deprotonation mechanism, determined the site‐selectivity of the transformation. The regioselectivity was controlled by the pKa of the C−H bond (more acidic position) and the lower distortion of chlorobenzene in the key transition structure. [ABSTRACT FROM AUTHOR] |
| Databáze: |
Complementary Index |
| Externí odkaz: |
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