Literature DB >> 10993364

Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide

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Abstract

Palladium-catalyzed cross-coupling of aryl- or alkenylsilanols, silanediols, and silanetriols with a variety of iodoarenes by the catalysis of palladium(0) and in the presence of silver(I) oxide furnished the coupling products in good to excellent yields. The reactions of silanediols or silanetriols under similar conditions proceeded much faster than those of silanols to afford the corresponding coupling products in excellent yields within shorter reaction periods (5-12 h). The measurement of the X-ray diffraction (XRD) pattern of the silver residue after the reaction revealed that silver(I) oxide was converted to silver(I) iodide.

Entities:  

Year:  2000        PMID: 10993364     DOI: 10.1021/jo000679p

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  Why You Really Should Consider Using Palladium-Catalyzed Cross-Coupling of Silanols and Silanolates.

Authors:  Scott E Denmark; Andrea Ambrosi
Journal:  Org Process Res Dev       Date:  2015       Impact factor: 3.317

2.  Phosphine Oxides as Stabilizing Ligands for the Palladium-Catalyzed Cross-Coupling of Potassium Aryldimethylsilanolates.

Authors:  Scott E Denmark; Russell C Smith; Steven A Tymonko
Journal:  Tetrahedron       Date:  2007-06-25       Impact factor: 2.457

3.  Silver-mediated fluorination of aryl silanes.

Authors:  Pingping Tang; Tobias Ritter
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

4.  Vinyl Tris(trimethylsilyl)silanes: Substrates for Hiyama Coupling.

Authors:  Zhizhong Wang; Jean-Philippe Pitteloud; Lucresia Montes; Magdalena Rapp; Djenny Derane; Stanislaw F Wnuk
Journal:  Tetrahedron       Date:  2008-05-26       Impact factor: 2.457

5.  Gold-catalyzed oxidative coupling reactions with aryltrimethylsilanes.

Authors:  William E Brenzovich; Jean-François Brazeau; F Dean Toste
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

6.  Cross-coupling reactions of aromatic and heteroaromatic silanolates with aromatic and heteroaromatic halides.

Authors:  Scott E Denmark; Russell C Smith; Wen-Tau T Chang; Joseck M Muhuhi
Journal:  J Am Chem Soc       Date:  2009-03-04       Impact factor: 15.419

7.  Regioselective allene hydroarylation via one-pot allene hydrosilylation/Pd-catalyzed cross-coupling.

Authors:  Zachary D Miller; John Montgomery
Journal:  Org Lett       Date:  2014-10-02       Impact factor: 6.005

  7 in total

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