Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes.

Autor: Dutta, Bishal, Mahajan, Mayank, Ghosh, Animesh, Dajek, Maciej, Kowalczyk, Rafal, Mondal, Bhaskar, Ge, Haibo, Maiti, Debabrata
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Zdroj: Nature Communications; 8/30/2024, Vol. 15 Issue 1, p1-9, 9p
Abstrakt: Regioselective distal C−H functionalization of nitroarenes by overriding proximal C−H activation has remained an unsolved challenge. Herein, we present a palladium-catalyzed meta-C−H alkenylation of nitroarene substrate, achieved through leveraging the non-covalent hydrogen bonding interactions. Urea-based templates comprising an elongated biphenyl linker designed in such a way that it interacts with nitro group via strong hydrogen bonding interaction, while a cyano based directing group is attached along the template to coordinate with the palladium center, thereby facilitating the activation of the remote meta-C−H bond of nitrobenzene. Computational mechanistic investigation and the analysis of non-covalent interaction deciphers the crucial role of H-bonding in regulating the regioselectivity. Regioselective distal C-H functionalization of nitroarenes by overriding proximal C-H activation has remained an unsolved challenge. Herein, the authors present a palladium-catalyzed meta-C-H alkenylation of nitroarene substrate, achieved through leveraging the noncovalent hydrogen bonding interactions. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index