Ru3(CO)12-catalyzed silylation of benzylic C-H bonds in arylpyridines and arylpyrazoles with hydrosilanes via C-H bond cleavage

Fumitoshi Kakiuchi; Kazuyuki Tsuchiya; Mitsutaka Matsumoto; Eiichiro Mizushima; Naoto Chatani

doi:10.1021/ja047040d

Ru3(CO)12-catalyzed silylation of benzylic C-H bonds in arylpyridines and arylpyrazoles with hydrosilanes via C-H bond cleavage

J Am Chem Soc. 2004 Oct 13;126(40):12792-3. doi: 10.1021/ja047040d.

Authors

Fumitoshi Kakiuchi¹, Kazuyuki Tsuchiya, Mitsutaka Matsumoto, Eiichiro Mizushima, Naoto Chatani

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan. kakiuchi@chem.eng.osaka-u.ac.jp

PMID: 15469271
DOI: 10.1021/ja047040d

Abstract

Ruthenium-catalyzed silylation of sp3 C-H bonds at a benzylic position with hydrosilanes gave benzylsilanes. For this silylation reaction, Ru3(CO)12 complex showed high catalytic activity. This silylation proceeded at the methyl C-H bond selectively. For this silylation reaction, pyridyl and pyrazolyl groups, and the imino group in hydrazones, can function as a directing group. Several hydrosilanes involving triethyl-, dimethylphenyl-, tert-butyldimethyl-, and triphenylsilanes can be used as a silylating reagent. Coordination of an sp2 nitrogen atom to the ruthenium complex is important for achieving this silylation reaction.