Literature DB >> 15469271

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

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

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.

Entities:  

Year:  2004        PMID: 15469271     DOI: 10.1021/ja047040d

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  15 in total

1.  Efficient iridium-catalyzed C-H functionalization/silylation of heteroarenes.

Authors:  Biao Lu; John R Falck
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  Silylation reactions on nanoporous gold via homolytic Si-H activation of silanes.

Authors:  Hongbo Li; Huifang Guo; Zhiwen Li; Cai Wu; Jing Li; Chunliang Zhao; Shuangxi Guo; Yi Ding; Wei He; Yadong Li
Journal:  Chem Sci       Date:  2018-04-30       Impact factor: 9.825

3.  A Chiral Nitrogen Ligand for Enantioselective, Iridium-Catalyzed Silylation of Aromatic C-H Bonds.

Authors:  Bo Su; Tai-Gang Zhou; Xian-Wei Li; Xiao-Ru Shao; Pei-Lin Xu; Wen-Lian Wu; John F Hartwig; Zhang-Jie Shi
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-15       Impact factor: 15.336

4.  Ir-Catalyzed Enantioselective, Intramolecular Silylation of Methyl C-H Bonds.

Authors:  Bo Su; John F Hartwig
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

5.  Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols.

Authors:  Caleb Karmel; Bijie Li; John F Hartwig
Journal:  J Am Chem Soc       Date:  2018-01-22       Impact factor: 15.419

6.  Fused heteroaromatic dihydrosiloles: synthesis and double-fold modification.

Authors:  Alexey Kuznetsov; Yoshiharu Onishi; Yoshihiro Inamoto; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2013-04-29       Impact factor: 6.005

7.  Iridium-Catalyzed Silylation of Unactivated C-H Bonds.

Authors:  John F Hartwig; Erik A Romero
Journal:  Tetrahedron       Date:  2019-05-27       Impact factor: 2.457

8.  Scope and mechanistic study of the ruthenium-catalyzed ortho-C-H bond activation and cyclization reactions of arylamines with terminal alkynes.

Authors:  Chae S Yi; Sang Young Yun
Journal:  J Am Chem Soc       Date:  2005-12-07       Impact factor: 15.419

9.  Silylation of C-H bonds in aromatic heterocycles by an Earth-abundant metal catalyst.

Authors:  Anton A Toutov; Wen-Bo Liu; Kerry N Betz; Alexey Fedorov; Brian M Stoltz; Robert H Grubbs
Journal:  Nature       Date:  2015-02-05       Impact factor: 49.962

Review 10.  A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.

Authors:  Carlo Sambiagio; David Schönbauer; Remi Blieck; Toan Dao-Huy; Gerit Pototschnig; Patricia Schaaf; Thomas Wiesinger; Muhammad Farooq Zia; Joanna Wencel-Delord; Tatiana Besset; Bert U W Maes; Michael Schnürch
Journal:  Chem Soc Rev       Date:  2018-08-28       Impact factor: 54.564

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