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https://doi.org/10.1021/cr500380d

Metal-mediated and metal-catalyzed reactions of isocyanides.

Mar 5, 2015
Chemical Reviews
Vadim P Boyarskiy +3 more

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ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTMetal-Mediated and Metal-Catalyzed Reactions of IsocyanidesVadim P. Boyarskiy*, Nadezhda A. Bokach*, Konstantin V. Luzyanin*, and Vadim Yu. Kukushkin*View Author Information Institute of Chemistry, Saint Petersburg State University, 198504 Stary Petergof, Russian Federation*E-mail: [email protected]*E-mail: [email protected]*E-mail: [email protected]*E-mail: [email protected]Cite this: Chem. Rev. 2015, 115, 7, 2698–2779Publication Date (Web):March 5, 2015Publication History Received14 July 2014Published online5 March 2015Published inissue 8 April 2015https://pubs.acs.org/doi/10.1021/cr500380dhttps://doi.org/10.1021/cr500380dreview-articleACS PublicationsCopyright © 2015 American Chemical SocietyRequest reuse permissionsArticle Views11586Altmetric-Citations444LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Addition reactions,Hydrocarbons,Inorganic carbon compounds,Ligands,Metals Get e-Alerts

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Gold Metal-Catalyzed Reactions of Isocyanides with Primary Amines and Oxygen: Analogies with Reactions of Isocyanides in Transition Metal Complexes

Jul 25, 2006
Journal of the American Chemical Society
Mihaela Lazar + 1 more

Despite its generally poor catalytic properties, bulk gold metal is observed to catalyze reactions of isocyanides (CN-R) with primary amines (H2N-R') and O2 to give carbodiimides (R-N=C=N-R') at room temperature and above. Detailed infrared reflection absorption spectroscopic (IRRAS) and kinetic studies show that the reaction occurs by initial eta1-adsorption of the isocyanide on the Au surface, which activates the isocyanide to attack by the amine. This attack is the rate-determining step in the catalytic cycle and has characteristics very similar to those of amine reactions with coordinated isocyanides in transition metal complexes. However, the metallic Au surface provides a pathway involving O2 to give the carbodiimide product whereas homogeneous metal ion catalysts give formamidines [HC(=NR)(NHR')].

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