Ruthenium Catalyst for Base-Free Synthesis of N-Silyl Enamines

A ruthenium complex, [(DmpSR')RuCl(P-(i-Pr)₃)], was reported to catalyze the N-silylation of imines.¹⁾ Because the catalyst activates the Si-H bond of silane, this reaction does not require addition of a base. Furthermore, it can proceed at room temperature with a low amount of catalyst. By dropwise addition of a solution of imine 1 and dimethylphenylsilane into a solution containing [(DmpSR')RuCl(P-(i-Pr)₃)] and NaBAr^F₄, both the N-silyl enamine 2 as a main product and 3 as a byproduct are afforded. Furthermore, the regioselective C-H silylation of indoles using this catalyst has also been reported.²⁾

Related Products

C3327

[(DmpSR')RuCl(P-(i-Pr)₃)]

D2196

Dimethylphenylsilane

S0447

NaBAr^F₄

References

• 1) Direct Catalytic Access to N-Silylated Enamines from Enolizable Imines and Hydrosilanes by Base-Free Dehydrogenative Si-N Coupling
  • J. Hermeke, H. F. T. Klare, M. Oestreich, Chem. Eur. J. 2014, 20, 9250.
• 2) Cooperative Catalytic Activation of Si-H Bonds by a Polar Ru-S Bond: Regioselective Low-Temperature C-H Silylation of Indoles under Neutral Conditions by a Friedel-Crafts Mechanism
  • H. F. T. Klare, M. Oestreich, J. Ito, H. Nishiyama, Y. Ohki, K. Tatsumi, J. Am. Chem. Soc. 2011, 133, 3312.

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