Hydrogen bonding template enables remote meta-C–H alkenylation of nitroarenes with electron-deficient alkenes
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.
Authors
- Bishal Dutta (ORCID: https://orcid.org/0009-0004-4777-2574)
- MaryAnn Mahajan (ORCID: https://orcid.org/0000-0003-1024-6808)
- Debabrata Maiti (ORCID: https://orcid.org/0000-0001-8353-1306)
- Haibo Ge (ORCID: https://orcid.org/0000-0001-6727-4602)
- Bhaskar Mondal (ORCID: https://orcid.org/0000-0001-9026-5974)
- Maciej Dajek (ORCID: https://orcid.org/0000-0002-7955-6743)
- Animesh Ghosh (ORCID: https://orcid.org/0000-0001-7391-9315)
- Rafał Kowalczyk (ORCID: https://orcid.org/0000-0001-5228-9131)
Institutions
- Wrocław University of Science and Technology (PL)
- Texas Tech University (US)
- Indian Institute of Technology Bombay (IN)
- University of Wrocław (PL)
- AGH University of Krakow (PL)
- Indian Institute of Technology Mandi (IN)
Publication Details
- Journal
- Nature Communications
- Published
- 2024-08-30
- DOI
- https://doi.org/10.1038/s41467-024-51764-1
- Citations
- 9
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.25
Funders
- National Science Foundation
- Texas Tech University
- Department of Science and Technology, Ministry of Science and Technology, India
- Indian Institute of Technology Madras
- Narodowe Centrum Nauki
- Ministry of Education, India
- Indian Institute of Technology Bombay
- Ministry of Electronics and Information technology
- Indian Institute of Technology Mandi
- Science and Engineering Research Board
- Division of Chemistry