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Defluorosilylation of Trifluoromethane: Upgrading an Environmentally Damaging Fluorocarbon

preprint
submitted on 17.08.2020 and posted on 18.08.2020 by Daniel Sheldon, Greg Coates, Mark Crimmin

The rapid, room-temperature defluorosilylation of trifluoromethane, a highly potent greenhouse gas, has been achieved using a simple silyl lithium reagent. An extensive computational mechanistic analysis provides a viable reaction pathway and demonstrates the unexpected electrophilic nature of LiCF3. The reaction generates a bench stable fluorinated building block that shows promise as an easy-to-use difluoromethylating agent. The difluoromethyl group is an increasingly important bioisostere in active pharmaceutical ingredients, and therefore our methodology creates value from waste. The potential scalability of the process has been demonstrated by achieving the reaction on a gram-scale.

Funding

ERC StG FluoroFix 677367

History

Email Address of Submitting Author

m.crimmin@imperial.ac.uk

Institution

Imperial College London

Country

United Kingdom

ORCID For Submitting Author

0000-0002-9339-9182

Declaration of Conflict of Interest

There are no conflicts to declare.

Version Notes

Version 1.1

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