Catalytic 1,4-Selective Hydrosilylation of Pyridines and Benzannulated Congeners†
Dipl.-Chem. C. David F. Königs
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de
Search for more papers by this authorDr. Hendrik F. T. Klare
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de
Search for more papers by this authorCorresponding Author
Prof. Dr. Martin Oestreich
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de===Search for more papers by this authorDipl.-Chem. C. David F. Königs
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de
Search for more papers by this authorDr. Hendrik F. T. Klare
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de
Search for more papers by this authorCorresponding Author
Prof. Dr. Martin Oestreich
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 115, 10623 Berlin (Germany) http://www.organometallics.tu-berlin.de===Search for more papers by this authorThis research was supported by the Technische Universität Berlin. M.O. is indebted to the Einstein Foundation (Berlin) for an endowed professorship.
Graphical Abstract
Radically different! The hydrosilylation of pyridines and quinolines is strictly 1,4-selective and likely involves an ionic one-step rather than the established radical two-step hydride transfer from a ruthenium(II) hydride complex onto the respective pyridinium and quinolinium ion intermediates (see scheme; ArF=3,5-(CF3)2C6H3). Even 4-substituted substrates react highly regioselectively. Isoquinolines yield the 1,2-reduced heterocycles.
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