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Cross‐Coupling of Nonactivated Alkyl Halides with Alkynyl Grignard Reagents: A Nickel Pincer Complex as the Catalyst

2011; Wiley; Volume: 50; Issue: 49 Linguagem: Inglês

10.1002/anie.201105964

ISSN

1521-3773

Autores

O. Vechorkin, Aurélien Godinat, Rosario Scopelliti, Xile Hu,

Tópico(s)

Cyclopropane Reaction Mechanisms

Resumo

Angewandte Chemie International EditionVolume 50, Issue 49 p. 11777-11781 Communication Cross-Coupling of Nonactivated Alkyl Halides with Alkynyl Grignard Reagents: A Nickel Pincer Complex as the Catalyst† Dr. Oleg Vechorkin, Dr. Oleg Vechorkin Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this authorAurélien Godinat, Aurélien Godinat Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this authorDr. Rosario Scopelliti, Dr. Rosario Scopelliti Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this authorProf. Dr. Xile Hu, Corresponding Author Prof. Dr. Xile Hu [email protected] Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chInstitute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this author Dr. Oleg Vechorkin, Dr. Oleg Vechorkin Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this authorAurélien Godinat, Aurélien Godinat Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this authorDr. Rosario Scopelliti, Dr. Rosario Scopelliti Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this authorProf. Dr. Xile Hu, Corresponding Author Prof. Dr. Xile Hu [email protected] Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chInstitute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), SB-ISIC-LSCI, BCH 3305, Lausanne, CH 1015 (Switzerland) http://lsci.epfl.chSearch for more papers by this author First published: 13 October 2011 https://doi.org/10.1002/anie.201105964Citations: 107 † This work is supported by the Swiss National Science Foundation (project no. 200021_126498). Read 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 onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract In a pinch: The nickel pincer complex 1 catalyzes the cross-coupling of the title compounds with remarkable substrate scope and functional group tolerance. A nickel/alkynyl species was isolated and shown to be catalytically competent. THF=tetrahydrofuran, O-TMEDA=bis[2-(N,N-dimethylaminoethyl)] ether. 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 anie_201105964_sm_miscellaneous_information.pdf6.9 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. References 1 Chemistry of Triple-Bonded Functional Groups (Eds.: ), Wiley, New York, 1994. 2 Modern Acetylene Chemistry (Eds.: ), VCH, Weinheim, 1995. 3R. Huisgen, Angew. Chem. 1963, 75, 604–637. 4H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056–2075; Angew. Chem. Int. Ed. 2001, 40, 2004–2021. 5M. Eckhardt, G. C. Fu, J. Am. Chem. Soc. 2003, 125, 13642–13643. 6G. Altenhoff, S. Wurtz, F. Glorius, Tetrahedron Lett. 2006, 47, 2925–2928. 7O. Vechorkin, D. Barmaz, V. Proust, X. L. Hu, J. Am. Chem. 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These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. Citing Literature Volume50, Issue49December 2, 2011Pages 11777-11781 ReferencesRelatedInformation

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