A review of frustrated Lewis pair enabled monoselective C-F bond activation

Abstract

Frustrated Lewis pair (FLP) bond activation chemistry has greatly developed over the last two decades since the seminal report of metal-free reversible hydrogen activation. Recently, FLP systems have been utilized to allow monoselective C-F bond activation (at equivalent sites) in polyfluoroalkanes. The problem of ‘over-defluorination’ in the functionalization of polyfluoroalkanes (where multiple fluoro-positions are uncontrollably functionalized) has been a long-standing chemical problem in fluorocarbon chemistry for over 80 years. FLP mediated monoselective C-F bond activation is complementary to other solutions developed to address ‘over-defluorination’ and offers several advantages and unique opportunities. This perspective highlights some of these advantages and opportunities and places the development of FLP mediated C-F bond activation into the context of the wider effort to overcome ‘over-defluorination’.