Muller, K., Faeh, C. & Diederich, F. Fluorine in pharmaceuticals: looking beyond intuition. Science 317, 1881–1886 (2007).

Article  PubMed  Google Scholar 

Berger, R., Resnati, G., Metrangolo, P., Weber, E. & Hulliger, J. Organic fluorine compounds: a great opportunity for enhanced materials properties. Chem. Soc. Rev. 40, 3496–3508 (2011).

Article  PubMed  CAS  Google Scholar 

Li, M., Xue, X. S. & Cheng, J. P. Establishing cation and radical donor ability scales of electrophilic F, CF3, and SCF3 transfer reagents. Acc. Chem. Res. 53, 182–197 (2020).

Article  PubMed  Google Scholar 

Xiao, P., Pannecoucke, X., Bouillon, J. P. & Couve-Bonnaire, S. Wonderful fusion of organofluorine chemistry and decarboxylation strategy. Chem. Soc. Rev. 50, 6094–6151 (2021).

Article  PubMed  CAS  Google Scholar 

He, M., Soulé, J.-F. & Doucet, H. Synthesis of (poly)fluorobiphenyls through metal-catalyzed C−H bond activation/arylation of (poly)fluorobenzene derivatives. ChemCatChem 6, 1824–1859 (2014).

Article  CAS  Google Scholar 

He, C.-Y., Fan, S. & Zhang, X. Pd-catalyzed oxidative cross-coupling of perfluoroarenes with aromatic heterocycles. J. Am. Chem. Soc. 132, 12850–12852 (2010).

Article  PubMed  CAS  Google Scholar 

Amii, H. & Uneyama, K. C–F bond activation in organic synthesis. Chem. Rev. 109, 2119–2183 (2009).

Article  PubMed  CAS  Google Scholar 

Eisenstein, O., Milani, J. & Perutz, R. N. Selectivity of C–H activation and competition between C–H and C–F bond activation at fluorocarbons. Chem. Rev. 117, 8710–8753 (2017).

Article  PubMed  CAS  Google Scholar 

Senaweera, S. M., Singh, A. & Weaver, J. D. Photocatalytic hydrodefluorination: facile access to partially fluorinated aromatics. J. Am. Chem. Soc. 136, 3002–3005 (2014).

Article  PubMed  CAS  Google Scholar 

Chen, Y. J. et al. Transition-metal-free, site-selective C–F arylation of polyfluoroarenes via electrophotocatalysis. J. Am. Chem. Soc. 144, 17261–17268 (2022).

Article  PubMed  CAS  Google Scholar 

Arora, A. & Weaver, J. D. Visible light photocatalysis for the generation and use of reactive azolyl and polyfluoroaryl intermediates. Acc. Chem. Res. 49, 2273–2283 (2016).

Article  PubMed  CAS  Google Scholar 

Qin, J., Zhu, S. Q. & Chu, L. L. Dual photoredox-/palladium-catalyzed cross-electrophile couplings of polyfluoroarenes with aryl halides and triflates. Organometallics 40, 2246–2252 (2021).

Article  CAS  Google Scholar 

Dewanji, A., Bulow, R. F. & Rueping, M. Photoredox/nickel dual-catalyzed reductive cross coupling of aryl halides using an organic reducing agent. Org. Lett. 22, 1611–1617 (2020).

Article  PubMed  CAS  Google Scholar 

Senaweera, S. & Weaver, J. D. Dual C–F, C–H functionalization via photocatalysis: access to multifluorinated biaryls. J. Am. Chem. Soc. 138, 2520–2523 (2016).

Article  PubMed  PubMed Central  CAS  Google Scholar 

Ahrens, T., Kohlmann, J., Ahrens, M. & Braun, T. Functionalization of fluorinated molecules by transition-metal-mediated C–F bond activation to access fluorinated building blocks. Chem. Rev. 115, 931–972 (2015).

Article  PubMed  CAS  Google Scholar 

Diccianni, J. B. & Diao, T. N. Mechanisms of nickel-catalyzed cross-coupling reactions. Trends Chem. 1, 830–844 (2019).

Article  CAS  Google Scholar 

Liu, X. W., Echavarren, J., Zarate, C. & Martin, R. Ni-catalyzed borylation of aryl fluorides via C–F cleavage. J. Am. Chem. Soc. 137, 12470–12473 (2015).

Article  PubMed  CAS  Google Scholar 

Zhou, J. et al. Preparing (multi)fluoroarenes as building blocks for synthesis: nickel-catalyzed borylation of polyfluoroarenes via C–F bond cleavage. J. Am. Chem. Soc. 138, 5250–5253 (2016).

Article  PubMed  CAS  Google Scholar 

Schaub, T. et al. C−F activation of fluorinated arenes using NHC-stabilized nickel(0) complexes: selectivity and mechanistic investigations. J. Am. Chem. Soc. 130, 9304–9317 (2008).

Article  PubMed  CAS  Google Scholar 

Nakamura, Y., Yoshikai, N., Ilies, L. & Nakamura, E. Nickel-catalyzed monosubstitution of polyfluoroarenes with organozinc reagents using alkoxydiphosphine ligand. Org. Lett. 14, 3316–3319 (2012).

Article  PubMed  CAS  Google Scholar 

Clot, E. et al. C−F and C−H bond activation of fluorobenzenes and fluoropyridines at transition metal centers: how fluorine tips the scales. Acc. Chem. Res. 44, 333–348 (2011).

Article  PubMed  CAS  Google Scholar 

Schaub, T., Backes, M. & Radius, U. Square-planar (pentafluorophenyl)nickel(II) complexes by derivatization of a C–F activation product. Eur. J. Inorg. Chem. 17, 2680–2690 (2008).

Article  Google Scholar 

Braun, T. & Perutz, R. N. Routes to fluorinated organic derivatives by nickel mediated C–F activation of heteroaromatics. Chem. Commun. 2749−2757 (2002).

Wang, K. & Kong, W. Synthesis of fluorinated compounds by nickel-catalyzed defluorinative cross-coupling reactions. ACS Catal. 13, 12238–12268 (2023).

Article  CAS  Google Scholar 

Ren, J.-A. et al. Nickel-catalyzed direct cross-coupling of unactivated aryl fluorides with aryl bromides. Org. Lett. 25, 5525–5529 (2023).

Article  PubMed  CAS  Google Scholar 

Das, A. & Chatani, N. The directing group: a tool for efficient and selective C–F bond activation. ACS Catal. 11, 12915–12930 (2021).

Article  CAS  Google Scholar 

Sun, A. D. & Love, J. A. Nickel-catalyzed selective defluorination to generate partially fluorinated biaryls. Org. Lett. 13, 2750–2753 (2011).

Article  PubMed  CAS  Google Scholar 

Capdevila, L. et al. Chemodivergent nickel(0)-catalyzed arene C–F activation with alkynes: unprecedented C–F/C–H double insertion. ACS Catal. 9, 11074–11081 (2019).

Article  CAS  Google Scholar 

Kuntze-Fechner, M. W. et al. Coligand role in the NHC nickel catalyzed C–F bond activation: investigations on the insertion of bis(NHC) nickel into the C–F bond of hexafluorobenzene. Chem. Sci. 11, 11009–11023 (2020).

Article  PubMed  PubMed Central  CAS  Google Scholar 

Doster, M. E. & Johnson, S. A. Selective C–F bond activation of tetrafluorobenzenes by nickel(0) with a nitrogen donor analogous to N-heterocyclic carbenes. Angew. Chem. Int. Ed. 48, 2185–2187 (2009).

Article  CAS  Google Scholar 

Doster, M. E., Hatnean, J. A., Jeftic, T., Modi, S. & Johnson, S. A. Catalytic C-H bond stannylation: a new regioselective pathway to C−Sn bonds via C-H bond functionalization. J. Am. Chem. Soc. 132, 11923–11925 (2010).

Article  PubMed  CAS  Google Scholar 

Butcher, T. W. et al. Desymmetrization of difluoromethylene groups by C–F bond activation. Nature 583, 548–553 (2020).

Article  PubMed  PubMed Central  CAS  Google Scholar 

Ohashi, M. et al. Palladium-catalyzed coupling reactions of tetrafluoroethylene with arylzinc compounds. J. Am. Chem. Soc. 133, 3256–3259 (2011).

Article  PubMed  CAS  Google Scholar 

Luo, Y. C., Wang, M. K., Yu, L. C. & Zhang, X. Nickel-catalyzed selective C(sp2)−F bond alkylation of industrially relevant hydrofluoroolefin HFO-1234yf. Angew. Chem. Int. Ed. 62, e202308690 (2023).

Article  CAS