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Catalytic 1,4‐Selective Hydrosilylation of Pyridines and Benzannulated Congeners
Author(s) -
Königs C. David F.,
Klare Hendrik F. T.,
Oestreich Martin
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201305028
Subject(s) - hydrosilylation , pyridinium , hydride , chemistry , catalysis , yield (engineering) , ruthenium , ionic bonding , medicinal chemistry , organic chemistry , ion , combinatorial chemistry , materials science , hydrogen , metallurgy
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; Ar F =3,5‐(CF 3 ) 2 C 6 H 3 ). Even 4‐substituted substrates react highly regioselectively. Isoquinolines yield the 1,2‐reduced heterocycles.