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Highly Efficient Ambient‐Temperature Copper‐Catalyzed Atom‐Transfer Radical Addition (ATRA) in the Presence of Free‐Radical Initiator (V‐70) as a Reducing Agent

2008; Wiley; Volume: 15; Issue: 1 Linguagem: Inglês

10.1002/chem.200802048

1521-3765

Tomislav Pintauer, William T. Eckenhoff, Carolynne Ricardo, Marielle Nicole C. Balili, A.B. Biernesser, Sean J. Noonan, Matthew J. Taylor,

Advanced Polymer Synthesis and Characterization

Chemistry – A European JournalVolume 15, Issue 1 p. 38-41 Communication Highly Efficient Ambient-Temperature Copper-Catalyzed Atom-Transfer Radical Addition (ATRA) in the Presence of Free-Radical Initiator (V-70) as a Reducing Agent Tomislav Pintauer Prof., Tomislav Pintauer Prof. pintauert@duq.edu Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorWilliam T. Eckenhoff, William T. Eckenhoff Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorCarolynne Ricardo, Carolynne Ricardo Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorMarielle N. C. Balili, Marielle N. C. Balili Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorAshley B. Biernesser, Ashley B. Biernesser Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorSean J. Noonan, Sean J. Noonan Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorMatthew J. W. Taylor, Matthew J. W. Taylor Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this author Tomislav Pintauer Prof., Tomislav Pintauer Prof. pintauert@duq.edu Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorWilliam T. Eckenhoff, William T. Eckenhoff Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorCarolynne Ricardo, Carolynne Ricardo Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorMarielle N. C. Balili, Marielle N. C. Balili Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorAshley B. Biernesser, Ashley B. Biernesser Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorSean J. Noonan, Sean J. Noonan Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this authorMatthew J. W. Taylor, Matthew J. W. Taylor Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Avenue, 308 Mellon Hall, Pittsburgh, PA 15282 (USA), Fax: (+1) 412-396-5683Search for more papers by this author First published: 18 December 2008 https://doi.org/10.1002/chem.200802048Citations: 53Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat Abstract Copper can do it! Highly efficient ambient-temperature copper-catalyzed ATRA of polyhalogenated compounds to alkenes in the presence of free-radical initiator 2,2′-azobis(4-methoxy-2,4-dimethyl valeronitrile) (V-70) is reported. V-70 has been shown to be a very effective reducing agent, enabling selective formation of the ATRA product with α-olefins and highly active monomers, such as methyl acrylate, methyl methacrylate, and vinyl acetate, by using as little as 0.002 mol % of copper (see figure). Citing Literature Supporting Information Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Filename Description chem_200802048_sm_miscellaneous_information.pdf1.1 MB miscellaneous_information Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume15, Issue1December 22, 2008Pages 38-41 RelatedInformation