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A Convenient Catalytic Procedure for the Addition of Trimethylsilyl Cyanide to Functionalised Ketones, Mediated by InBr3 − Insight into the Reaction Mechanism

2002; Wiley; Volume: 2002; Issue: 19 Linguagem: Inglês

10.1002/1099-0690(200210)2002

1434-193X

Marco Bandini, Pier Giorgio Cozzi, Andrea Garelli, Paolo Melchiorre, Achille Umani‐Ronchi,

Synthesis and Catalytic Reactions

European Journal of Organic ChemistryVolume 2002, Issue 19 p. 3243-3249 Full Paper A Convenient Catalytic Procedure for the Addition of Trimethylsilyl Cyanide to Functionalised Ketones, Mediated by InBr3 − Insight into the Reaction Mechanism Marco Bandini, Marco Bandini bandini@ciam.unibo.it Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorPier Giorgio Cozzi, Pier Giorgio Cozzi Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorAndrea Garelli, Andrea Garelli Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorPaolo Melchiorre, Paolo Melchiorre Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorAchille Umani-Ronchi, Achille Umani-Ronchi umani@ciam.unibo.it Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this author Marco Bandini, Marco Bandini bandini@ciam.unibo.it Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorPier Giorgio Cozzi, Pier Giorgio Cozzi Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorAndrea Garelli, Andrea Garelli Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorPaolo Melchiorre, Paolo Melchiorre Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this authorAchille Umani-Ronchi, Achille Umani-Ronchi umani@ciam.unibo.it Dipartimento di Chimica "G. Ciamician" via Selmi 2, 40126 Bologna, Italy, Fax: (internat.) + 39-051/209-9456Search for more papers by this author First published: 20 September 2002 https://doi.org/10.1002/1099-0690(200210)2002:19 3.0.CO;2-ECitations: 56Read 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 onFacebookTwitterLinkedInRedditWechat Abstract This paper describes a useful and practical methodology for the addition of trimethylsilyl cyanide (TMSCN) to a large variety of functionalised and unfunctionalised ketones in the presence of catalytic amounts of anhydrous InBr3. The optimum procedure involves low catalyst loading (1 mol %) and appears general in scope and applicability for aromatic and aliphatic ketones. The desired cyanohydrins were typically isolated as their O-silyl ethers in good to excellent chemical yields (up to 99%). Kinetic and spectroscopic studies suggest that a catalytically active dimeric indium species is involved in the reaction mechanism. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002) Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2046/2002/o02264_s.pdf or from the author. 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. Volume2002, Issue19October 2002Pages 3243-3249 RelatedInformation