Literature DB >> 11009386

Mild and general cross-coupling of (alpha-Alkoxyvinyl)silanols and -silyl hydrides

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Abstract

(alpha-Alkoxyvinyl)silanols and (alpha-alkoxyvinyl)silyl hydrides are efficiently converted to aryl vinyl ethers by a palladium(0)-catalyzed cross-coupling reaction with aryl halides in the presence of tetrabutylammonium fluoride or hydroxide. Yields are generally high, and the reaction is compatible with a wide range of functional groups.

Entities:  

Year:  2000        PMID: 11009386     DOI: 10.1021/ol0064112

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


  12 in total

1.  Total Synthesis of (+)-Papulacandin D.

Authors:  Scott E Denmark; Tetsuya Kobayashi; Christopher S Regens
Journal:  Tetrahedron       Date:  2010-06-26       Impact factor: 2.457

2.  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

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.  The design, synthesis and validation of recoverable and readily reusable siloxane transfer agents for Pd-catalyzed cross-coupling reactions.

Authors:  Dionicio Martinez-Solorio; Adam T Hoye; Minh H Nguyen; Amos B Smith
Journal:  Org Lett       Date:  2013-04-29       Impact factor: 6.005

5.  The interplay of invention, discovery, development, and application in organic synthetic methodology: a case study.

Authors:  Scott E Denmark
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

6.  Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols.

Authors:  Scott E Denmark; Christopher R Butler
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

7.  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

8.  Palladium-catalyzed acetylation of arenes.

Authors:  Stephen D Ramgren; Neil K Garg
Journal:  Org Lett       Date:  2014-01-09       Impact factor: 6.005

9.  A well-defined NHC-Ir(iii) catalyst for the silylation of aromatic C-H bonds: substrate survey and mechanistic insights.

Authors:  Laura Rubio-Pérez; Manuel Iglesias; Julen Munárriz; Victor Polo; Vincenzo Passarelli; Jesús J Pérez-Torrente; Luis A Oro
Journal:  Chem Sci       Date:  2017-04-05       Impact factor: 9.825

10.  Direct catalytic cross-coupling of alkenyllithium compounds.

Authors:  Valentín Hornillos; Massimo Giannerini; Carlos Vila; Martín Fañanás-Mastral; Ben L Feringa
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

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