Abstract
Fluoroform, which is generated in ~20 kilotons/year as a side product of Teflon manufacture,[1] [2] is a low-boiling (-82 °C), non-toxic and non-ozone-depleting gas.[1,3] However, fluoroform is a potent greenhouse agent and there is great interest in methods for use of the gas as a synthetic reagent. The direct use of trifluoromethyl anion as a nucleophile has been challenging due to facile α-elimination to fluoride and difluorocarbene (Scheme [1]). The activation of Me3SiCF3 (often described as the Ruppert–Prakash reagent) with Lewis bases (most commonly catalytic fluoride) to afford pentavalent silicon species as nucleophiles has enabled trifluoromethylation of a number of electrophiles.[4] The trifluoromethyl group has great importance in medicinal, agrochemical and materials science.[5] This spotlight describes recently reported methods for tri- and difluoromethylation based upon fluoroform.
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