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Taking Advantage of the Ambivalent Reactivity of Ynamides in Gold Catalysis: A Rare Case of Alkyne Dimerization

2011; Wiley; Volume: 50; Issue: 22 Linguagem: Inglês

10.1002/anie.201100327

1521-3773

Søren Kramer, Yann Odabachian, Jacob Overgaard, Mario Rottländer, Fabien Gagosz, Troels Skrydstrup,

Synthetic Organic Chemistry Methods

Angewandte Chemie International EditionVolume 50, Issue 22 p. 5090-5094 Communication Taking Advantage of the Ambivalent Reactivity of Ynamides in Gold Catalysis: A Rare Case of Alkyne Dimerization† Søren Kramer, Søren Kramer Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this authorYann Odabachian, Yann Odabachian Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France)Search for more papers by this authorDr. Jacob Overgaard, Dr. Jacob Overgaard Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this authorDr. Mario Rottländer, Dr. Mario Rottländer Division of Medicinal Chemistry, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby (Denmark)Search for more papers by this authorDr. Fabien Gagosz, Corresponding Author Dr. Fabien Gagosz gagosz@dcso.polytechnique.fr Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France) Fabien Gagosz, Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France) Troels Skrydstrup, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this authorProf. Troels Skrydstrup, Corresponding Author Prof. Troels Skrydstrup ts@chem.au.dk Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark) Fabien Gagosz, Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France) Troels Skrydstrup, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this author Søren Kramer, Søren Kramer Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this authorYann Odabachian, Yann Odabachian Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France)Search for more papers by this authorDr. Jacob Overgaard, Dr. Jacob Overgaard Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this authorDr. Mario Rottländer, Dr. Mario Rottländer Division of Medicinal Chemistry, H. Lundbeck A/S, Ottiliavej 9, 2500 Valby (Denmark)Search for more papers by this authorDr. Fabien Gagosz, Corresponding Author Dr. Fabien Gagosz gagosz@dcso.polytechnique.fr Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France) Fabien Gagosz, Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France) Troels Skrydstrup, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this authorProf. Troels Skrydstrup, Corresponding Author Prof. Troels Skrydstrup ts@chem.au.dk Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark) Fabien Gagosz, Département de Chimie, UMR 7652 CNRS, Ecole Polytechnique, 91128 Palaiseau (France) Troels Skrydstrup, Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C (Denmark)Search for more papers by this author First published: 19 April 2011 https://doi.org/10.1002/anie.201100327Citations: 99 † We are deeply appreciative of generous financial support from the Carlsberg Foundation, the Danish National Research Foundation, H. Lundbeck A/S, the OChem Graduate School, the Ecole Polytechnique and Aarhus University. 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 onFacebookTwitterLinked InRedditWechat Abstract A gold mine of results: A series of ynamides have been dimerized in the presence of a gold(I) complex. This unprecedented transformation involves the formation of a key keteniminium intermediate that reacts to form a variety of cyclic and acyclic products. The substitution pattern of the ynamide determines which product is formed (see scheme; EWG=electron-withdrawing group, Ts=p-toluenesulfonyl). 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 anie_201100327_sm_miscellaneous_information.pdf4.7 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. Volume50, Issue22May 23, 2011Pages 5090-5094 RelatedInformation