Aromatic trifluoromethyldenitration and trifluoromethyldecyanation using trifluoromethyltrimethylsilane

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Dave J. Adams, James H. Clark, Liv B. Hansen, Victoria C. Sanders and Stewart J. Tavener


Abstract

Activation of trifluoromethyltrimethylsilane by potassium fluoride in N,N-dimethylacetamide provides a powerful source of trifluoromethide which is capable of substituting aromatic nitro and cyano groups under nucleophilic conditions, albeit in low yield. The trifluoromethide generated in this system is also a potent base which leads to a number of interesting side reactions via deprotonation of the substrate.


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