Iridium-Catalyzed Regioselective C(sp3)–H Silylation of 4‑Alkylpyridines at the Benzylic Position with Hydrosilanes Leading to 4‑(1-Silylalkyl)pyridines

Iridium-Catalyzed Regioselective C(sp3)–H Silylation of 4‑Alkylpyridines at the Benzylic Position with Hydrosilanes Leading to 4‑(1-Silylalkyl)pyridines

The regioselective silylation of C­(sp3)–H bonds at the benzylic position in 4-alkylpyridines with hydrosilanes is described. The reaction proceeds in the presence of a catalytic amount of Ir4(CO)12 or Ir­(acac)­(CO)2, which possess CO as a ligand, or [Ir­(OMe)­(cod)]2 under 1 atm of CO. After optim...

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Veröffentlicht in:ACS catalysis 2017-05, Vol.7 (5), p.3152-3156
Hauptverfasser: Fukumoto, Yoshiya, Hirano, Masaya, Chatani, Naoto
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Chatani, Naoto
description The regioselective silylation of C­(sp3)–H bonds at the benzylic position in 4-alkylpyridines with hydrosilanes is described. The reaction proceeds in the presence of a catalytic amount of Ir4(CO)12 or Ir­(acac)­(CO)2, which possess CO as a ligand, or [Ir­(OMe)­(cod)]2 under 1 atm of CO. After optimizing the reaction conditions, by using other pyridine derivatives, such as 3,5-dimethylpyridine, as additives, the low product yields of 2-substituted 4-methylpyridines were improved markedly.
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