Literature DB >> 20509671

PyDipSi: a general and easily modifiable/traceless Si-tethered directing group for C-H acyloxylation of arenes.

Natalia Chernyak1, Alexander S Dudnik, Chunhui Huang, Vladimir Gevorgyan.   

Abstract

A new general and easily installable silicon-tethered pyridyl-containing directing group (PyDipSi) that allows for highly efficient and regioselective Pd-catalyzed ortho C-H acyloxylation of arenes has been developed. It has also been demonstrated that this directing group can efficiently be removed as well as converted into a variety of other valuable functional groups. In addition, the installation of the PyDipSi directing group along with pivaloxylation and quantitative conversion of the PyDipSi group into a halogen functionality represents a formal three-step ortho oxygenation of haloarenes.

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Year:  2010        PMID： 20509671      PMCID： PMC2891945          DOI： 10.1021/ja1033167

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


  51 in total

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2.  Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors:  Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
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3.  Enantioselective Addition of Allylic Trimethoxysilanes to Aldehydes Catalyzed by p-Tol-BINAP small middle dotAgF.

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4.  Directed ortho metalation-based methodology. Halo-, nitroso-, and boro-induced ipso-desilylation. Link to an in situ Suzuki reaction.

Authors:  Zhongdong Zhao; Victor Snieckus
Journal:  Org Lett       Date:  2005-06-23       Impact factor: 6.005

5.  Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles.

Authors:  Daniel W Robbins; Timothy A Boebel; John F Hartwig
Journal:  J Am Chem Soc       Date:  2010-03-31       Impact factor: 15.419

6.  Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: expedient routes to anthranilic acids, oxazolinones, and quinazolinones.

Authors:  Ramesh Giri; Jonathan K Lam; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

7.  Bimetallic palladium catalysis: direct observation of Pd(III)-Pd(III) intermediates.

Authors:  David C Powers; Matthias A L Geibel; Johannes E M N Klein; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2009-12-02       Impact factor: 15.419

8.  The direct use of phenyldimethylsilanes in silicon assisted palladium catalysed cross coupling.

Authors:  James C Anderson; Stéphane Anguille; Rosalyn Bailey
Journal:  Chem Commun (Camb)       Date:  2002-09-21       Impact factor: 6.222

Review 9.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Authors:  Egle M Beccalli; Gianluigi Broggini; Michela Martinelli; Silvia Sottocornola
Journal:  Chem Rev       Date:  2007-11-01       Impact factor: 60.622

10.  Cross-coupling reactions of aryl pivalates with boronic acids.

Authors:  Kyle W Quasdorf; Xia Tian; Neil K Garg
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419
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  16 in total

1.  Silicon-Tethered Strategies for C-H Functionalization Reactions.

Authors:  Marvin Parasram; Vladimir Gevorgyan
Journal:  Acc Chem Res       Date:  2017-08-03       Impact factor: 22.384

2.  Enantioselective Synthesis of β-Fluoro Amines via β-Amino α-Fluoro Nitroalkanes and a Traceless Activating Group Strategy.

Authors:  Brandon A Vara; Jeffrey N Johnston
Journal:  J Am Chem Soc       Date:  2016-10-17       Impact factor: 15.419

3.  Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.

Authors:  Chunhui Huang; Buddhadeb Chattopadhyay; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2011-07-21       Impact factor: 15.419

4.  General and practical carboxyl-group-directed remote C-H oxygenation reactions of arenes.

Authors:  Yang Wang; Anton V Gulevich; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2013-10-21       Impact factor: 5.236

5.  A general strategy toward aromatic 1,2-ambiphilic synthons: palladium-catalyzed ortho-halogenation of PyDipSi-arenes.

Authors:  Alexander S Dudnik; Natalia Chernyak; Chunhui Huang; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

6.  Double-fold C-H oxygenation of arenes using PyrDipSi: a general and efficient traceless/modifiable silicon-tethered directing group.

Authors:  Anton V Gulevich; Ferdinand S Melkonyan; Dhruba Sarkar; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2012-03-19       Impact factor: 15.419

7.  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

8.  Meta-selective C-H functionalization using a nitrile-based directing group and cleavable Si-tether.

Authors:  Sunggi Lee; Hyelee Lee; Kian L Tan
Journal:  J Am Chem Soc       Date:  2013-12-10       Impact factor: 15.419

9.  Pd-catalyzed modifiable silanol-directed aromatic C-H oxygenation.

Authors:  Chunhui Huang; Nugzar Ghavtadze; Benhur Godoi; Vladimir Gevorgyan
Journal:  Chemistry       Date:  2012-07-02       Impact factor: 5.236

10.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

Authors:  Chunhui Huang; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal:  Adv Synth Catal       Date:  2011-05-01       Impact factor: 5.837
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