Nickel(0)-Catalyzed C-F and C-H Activation in Fluorinated Compounds
Lorena Capdevila,1 Lutz Ackermann,2 Anna Company,1 and Xavi Ribas1* 1QBIS-CAT research group (IQCC), Universitat de Girona, Girona, Spain. 2Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Göttingen, Germany
Email: lorena.capdevila@udg.edu
Albeit the great interest in the synthesis of fluorinated compounds due to their enhanced metabolic stability, lipophilicity and bioavailability,[1] the selective activation of C-F over C-H is of interest in the detoxification of fluorinated compounds present in waste water. Nickel has emerged as one of the metal of choice due to its ability to activate C-F bonds.[2] Here we study the selective activation of C-F versus C-H bonds in fluorinated arene model compounds. The use of directing groups is crucial to achieve site-selective functionalization. Mechanistic insights of the aromatic homologation reaction are also discussed.
References
[1] Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886.
[2] Ahrens, T.; Kohlmann, J.; Ahrens, M.; Braun, T. Chem. Rev. 2015, 115, 931−972.