Exploring C-F Activation Chemistry of CF3-dienes for the Green Synthesis of New Fluorinated Building Blocks
Implementing Organization
Mohan Lal Sukhadia University, Rajasthan
Principal Investigator
Dr. Tarun Kumar
Mohan Lal Sukhadia University, Rajasthan
Project Overview
The functionalization of polyfluorinated compounds into partially fluorinated compounds through the cleavage of the C-F bond is a challenging task in the scientific community. Single C-F bond activation in CF3-alkenes is difficult due to the high bond dissociation energy for the first C-F bond, and as the number of fluorines on carbon decreases, the bond dissociation energy for subsequent C-F bonds decreases, potentially resulting in multiple C-F bond activations. This has led to a growing interest in single C-F bond activation in CF3-dienes. A new method is proposed for selective single C-F bond activation in CF3-dienes for the synthesis of fluorinated building blocks. The strategy involves using naturally abundant and cheap alkaline earth metals, which have a high negative value of reduction potential and can easily reduce CF3-dienes. The C-F bond activation process can be facilitated by the presence of TMSCl. The project's success is supported by preliminary results, including the isolation of the expected reaction imtermediate TMS-difluoroalkene and confirmation of C-F bond cleavage in CF3-diene (benzofulvene) by 19F NMR Spectroscopy. This simple, green, eco-friendly, and financially cheap method will be accessible to a large research community, offering a simple and green approach to selective single C-F bond cleavage in lesser explored trifluoromethyl-dienes.