Fig. 8: Mechanochemically driven C–F bond lithiation.

a, Mechanochemistry allows efficient C−F bond lithiation with bulk lithium metal. The photos show that lithium metal was completely pulverized under mechanochemical conditions, while some remains unreacted in the test tube reaction. b, Scope of organofluorine compounds. c, Selective stepwise functionalization via late-stage C−F bond lithiation. Isolated yields are shown. Integrated 1H NMR spectroscopic yields are shown in parentheses. dppf, 1,1′-bis(diphenylphosphino)ferrocene; acac, acetylacetonate; E+, electrophile; THF, tetrahydrofuran; NMP, N-methyl-2-pyrrolidone; r.t., room temperature. See Supplementary Sections 2 and 8 for details.