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

Bishal Dutta, Mayank Mahajan, Animesh Ghosh, Maciej Dajek, Rafal Kowalczyk (), Bhaskar Mondal (), Haibo Ge () and Debabrata Maiti ()
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Bishal Dutta: Indian Institute of Technology Bombay
Mayank Mahajan: Indian Institute of Technology Mandi
Animesh Ghosh: Indian Institute of Technology Bombay
Maciej Dajek: Wroclaw University of Science and Technology
Rafal Kowalczyk: Wroclaw University of Science and Technology
Bhaskar Mondal: Indian Institute of Technology Mandi
Haibo Ge: Texas Tech University
Debabrata Maiti: Indian Institute of Technology Bombay

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract 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.

Date: 2024
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DOI: 10.1038/s41467-024-51764-1

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