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. 2013 Sep 16;52(38):10076-9.
doi: 10.1002/anie.201305028. Epub 2013 Aug 1.

Catalytic 1,4-selective hydrosilylation of pyridines and benzannulated congeners

C David F Königs  1 , Hendrik F T Klare, Martin Oestreich
Affiliations

Catalytic 1,4-selective hydrosilylation of pyridines and benzannulated congeners

C David F Königs et al. Angew Chem Int Ed Engl. .

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; Ar(F) =3,5-(CF3)2C6H3). Even 4-substituted substrates react highly regioselectively. Isoquinolines yield the 1,2-reduced heterocycles.

Keywords: N-heterocycles; SiH bond activation; homogeneous catalysis; hydrosilylation; regioselectivity.

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