Literature DB >> 23305172

Rhodium-catalyzed intramolecular silylation of unactivated C(sp3)-H bonds.

Yoichiro Kuninobu1, Takahiro Nakahara, Hirotaka Takeshima, Kazuhiko Takai.   

Abstract

The treatment of a variety of hydrosilanes, each incorporating a benzylic C(sp(3))-H bond, with a rhodium catalyst resulted in intramolecular dehydrogenative silylation. This silylation reaction was found to occur at typically unreactive C(sp(3))-H bonds located at terminal positions on alkyl chains. Interestingly, the rhodium catalyst also promoted regioselective silylation at a site internal to an alkyl chain.

Entities:  

Year:  2013        PMID： 23305172     DOI： 10.1021/ol303353m

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  11 in total

1.  Rhodium-catalyzed enantioselective silylation of arene C-H bonds: desymmetrization of diarylmethanols.

Authors:  Taegyo Lee; Tyler W Wilson; Robert Berg; Per Ryberg; John F Hartwig
Journal:  J Am Chem Soc       Date:  2015-05-20       Impact factor: 15.419

2.  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

3.  General method for the synthesis of salicylic acids from phenols through palladium-catalyzed silanol-directed C-H carboxylation.

Authors:  Yang Wang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-19       Impact factor: 15.336

Review 4.  Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Authors:  Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal:  Chem Rev       Date:  2021-10-29       Impact factor: 60.622

5.  Catalytic Reductive ortho-C-H Silylation of Phenols with Traceless, Versatile Acetal Directing Groups and Synthetic Applications of Dioxasilines.

Authors:  Yuanda Hua; Parham Asgari; Thirupataiah Avullala; Junha Jeon
Journal:  J Am Chem Soc       Date:  2016-06-16       Impact factor: 15.419

6.  Rhodium-Catalyzed Enantioselective Silylation of Cyclopropyl C-H Bonds.

Authors:  Taegyo Lee; John F Hartwig
Journal:  Angew Chem Int Ed Engl       Date:  2016-06-02       Impact factor: 15.336

Review 7.  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

8.  Conversion of 1-alkenes into 1,4-diols through an auxiliary-mediated formal homoallylic C-H oxidation.

Authors:  Nugzar Ghavtadze; Ferdinand S Melkonyan; Anton V Gulevich; Chunhui Huang; Vladimir Gevorgyan
Journal:  Nat Chem       Date:  2014-01-19       Impact factor: 24.427

9.  Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinyl carboxylic acids via a radical process.

Authors:  Jiancan Zhao; Hong Fang; Jianlin Han; Yi Pan
Journal:  Beilstein J Org Chem       Date:  2013-08-21       Impact factor: 2.883

Review 10.  Preparative Synthesis of Highly Substituted Tetrahydropyridines via a Rh(I)-Catalyzed C-H Functionalization Sequence.

Authors:  Tehetena Mesganaw; Jonathan A Ellman
Journal:  Org Process Res Dev       Date:  2014-08-29       Impact factor: 3.317
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