Well‐Defined Cyclopentadienyl NHC Iron Complex as the Catalyst for Efficient Hydrosilylation of Amides to Amines and Nitriles

ChemCatChemVolume 3, Issue 11 p. 1747-1750 Communication Well-Defined Cyclopentadienyl NHC Iron Complex as the Catalyst for Efficient Hydrosilylation of Amides to Amines and Nitriles† David Bézier, David Bézier UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this authorDr. Gopaladasu T. Venkanna, Dr. Gopaladasu T. Venkanna UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this authorDr. Jean-Baptiste Sortais, Corresponding Author Dr. Jean-Baptiste Sortais [email protected] UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this authorProf. Dr. Christophe Darcel, Corresponding Author Prof. Dr. Christophe Darcel [email protected] UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this author David Bézier, David Bézier UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this authorDr. Gopaladasu T. Venkanna, Dr. Gopaladasu T. Venkanna UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this authorDr. Jean-Baptiste Sortais, Corresponding Author Dr. Jean-Baptiste Sortais [email protected] UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this authorProf. Dr. Christophe Darcel, Corresponding Author Prof. Dr. Christophe Darcel [email protected] UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39UMR 6226 CNRS-Université de Rennes 1, Sciences Chimiques de Rennes, Building 10C, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes (France), Fax: (+33) 2-23-23-69-39Search for more papers by this author First published: 30 August 2011 https://doi.org/10.1002/cctc.201100202Citations: 133 † NHC=N-Heterocyclic carbene. 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 Iron comes first, second, and third: By using the well-defined Cp-IMes iron cationic complex ([Fe], see scheme) as the catalyst, an efficient and versatile hydrosilylation reduction reaction of secondary and tertiary amides is performed in solvent-free conditions at 100 °C under visible light irradiation for 16 h to give the corresponding amines in good yields. When the reaction is performed with primary amides, the corresponding nitrile derivatives are obtained. 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 cctc_201100202_sm_miscellaneous_information.pdf4.6 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 1For a list of methods, see: 1aR. C. Larock, in Comprehensive Organic Transformations: A Guide to Functional Group Preparation, 2nd ed., Wiley-VCH, New York, 1989; 1bK. Weissermel, H. J. Arpe, Industrial Organic Chemistry, 4th ed., Wiley-VCH, Weinheim, 1997; 1cS. A. 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Darcel, 2011, unpublished results. 21In the reduction of N,N-diphenylbenzamide, even by using 4 equiv of phenylsilane, conversion reached only 40 % with 4 % of the desired product and 36 % of diphenylamine as the byproduct. Citing Literature Volume3, Issue11November 18, 2011Pages 1747-1750 ReferencesRelatedInformation