Mechanochemical McMurry reaction: deoxygenative reductive olefination of carbonyl using ball milling

Shirsath, Sakshi Ajay (2025) Mechanochemical McMurry reaction: deoxygenative reductive olefination of carbonyl using ball milling. Masters thesis, Indian Institute of Science Education and Research Kolkata.

Text (MS Dissertation of Sakshi Ajay Shirsath (20MS215)) 20MS215_Thesis_file.pdf - Submitted Version Restricted to Repository staff only Download (2MB)

Abstract

Developments in approaches that give atom economy and environmental remediation first priority have been fueled by the quest for sustainable chemistry. For organic transformations, mechanochemistry has proven to be a very successful solvent-free method with softer reaction conditions and shorter reaction durations. Targeting tetra-aryl ethylenes (TAEs), we investigate the mechanochemical modification of the McMurry coupling procedure to produce tetrasubstituted ethylenes (TSEs) in this work. Utilizing ball milling conditions with Zn/TiCl₄ and triethylamine as reagents, this method achieves up to 98% isolated yields and exhibits great efficiency with a wide substrate scope. In a Teflon milling jar, the reactions could be carried out without the use of inert gas protection. It is noteworthy that the reaction can tolerate certain functional groups and is scalable. This process offers a cost-effective and environmentally responsible technique to produce TSEs and demonstrates how mechanochemistry may promote green chemistry ideas and foster sustainable innovation.

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