Defluorosilylation of trifluoromethane: upgrading an environmentally damaging fluorocarbon

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 LiCF...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2020-11, Vol.56 (85), p.12929-12932
Main Authors: Sheldon, Daniel J, Coates, Greg, Crimmin, Mark R
Format: Article
Language:English
Subjects:
Greenhouse effect
Greenhouse gases
Lithium
Reagents
Room temperature
Trifluoromethane
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Summary: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 LiCF 3 . 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. The rapid, room-temperature defluorosilylation of trifluoromethane, a highly potent greenhouse gas, has been achieved using a simple silyl lithium reagent.
ISSN:1359-7345
1364-548X
DOI:10.1039/d0cc04592f