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Literature DB >> 12375906

A general and straightforward route toward diarylmethanes. Integrated cross-coupling reactions using (2-pyridyl)silylmethylstannane as an air-stable, storable, and versatile coupling platform.

Kenichiro Itami¹, Masahiro Mineno, Toshiyuki Kamei, Jun-Ichi Yoshida.

Abstract

[reaction: see text] Pharmacologically important diarylmethane structures have been prepared in a straightforward manner through sequentially integrated Pd-catalyzed cross-coupling reactions. (2-Pyridyl)silylmethylstannane was found to be an air-stable, storable, and versatile coupling platform in this synthetic strategy.

Entities: Chemical

Year: 2002 PMID： 12375906 DOI： 10.1021/ol026573t

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

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Cited

8 in total

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

Authors: Natalia Chernyak; Alexander S Dudnik; Chunhui Huang; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2010-06-23 Impact factor: 15.419

2. Arenechromiumtricarbonyl complexes of silyl(germyl)(stannyl)- and silyl(germyl)(plumbyl)methanes including unexpected formation of arenechromiumtricarbonyldimethylsilanol, (eta-C(6)H(5))Cr(CO)(3)SiMe(2)OH.

Authors: Hemant K Sharma; Francisco Cervantes-Lee; Keith H Pannell
Journal: J Organomet Chem Date: 2010-04-15 Impact factor: 2.369

3. 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

4. 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

5. 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

A general and straightforward route toward diarylmethanes. Integrated cross-coupling reactions using (2-pyridyl)silylmethylstannane as an air-stable, storable, and versatile coupling platform.

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

2. Arenechromiumtricarbonyl complexes of silyl(germyl)(stannyl)- and silyl(germyl)(plumbyl)methanes including unexpected formation of arenechromiumtricarbonyldimethylsilanol, (eta-C(6)H(5))Cr(CO)(3)SiMe(2)OH.

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

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

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

6. Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts.

7. Cobalt co-catalysis for cross-electrophile coupling: diarylmethanes from benzyl mesylates and aryl halides.

8. Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles.