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While fluoroaryl fragments are ubiquitous in many pharmaceuticals, the deprotonation of fluoroarenes using organolithium bases constitutes an important challenge in polar organometallic chemistry. This has been widely attributed to the low stability of the in situ generated aryl lithium intermediates that even at -78 °C can undergo unwanted side reactions. Herein, pairing lithium amide LiHMDS (HMDS = NSiMe₃₂) with FeII(HMDS)₂ enables the selective deprotonation at room temperature of pentafluorobenzene and 1,3,5-trifluorobenzene via the
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