1,2‐Migration of the Thio Group in Allenyl Sulfides: Efficient Synthesis of 3‐Thio‐Substituted Furans and Pyrroles

Angewandte Chemie International EditionVolume 42, Issue 1 p. 98-101 Communication 1,2-Migration of the Thio Group in Allenyl Sulfides: Efficient Synthesis of 3-Thio-Substituted Furans and Pyrroles† Joseph T. Kim, Joseph T. Kim Department of Chemistry, University of Illinois at Chicago 845 West Taylor Street, Chicago, IL 60607-7061, USA, Fax: (+1) 312-355-0836Search for more papers by this authorAlexander V. Kel'in, Alexander V. Kel'in Department of Chemistry, University of Illinois at Chicago 845 West Taylor Street, Chicago, IL 60607-7061, USA, Fax: (+1) 312-355-0836Search for more papers by this authorVladimir Gevorgyan Prof. Dr., Vladimir Gevorgyan Prof. Dr. vlad@uic.edu Department of Chemistry, University of Illinois at Chicago 845 West Taylor Street, Chicago, IL 60607-7061, USA, Fax: (+1) 312-355-0836Search for more papers by this author Joseph T. Kim, Joseph T. Kim Department of Chemistry, University of Illinois at Chicago 845 West Taylor Street, Chicago, IL 60607-7061, USA, Fax: (+1) 312-355-0836Search for more papers by this authorAlexander V. Kel'in, Alexander V. Kel'in Department of Chemistry, University of Illinois at Chicago 845 West Taylor Street, Chicago, IL 60607-7061, USA, Fax: (+1) 312-355-0836Search for more papers by this authorVladimir Gevorgyan Prof. Dr., Vladimir Gevorgyan Prof. Dr. vlad@uic.edu Department of Chemistry, University of Illinois at Chicago 845 West Taylor Street, Chicago, IL 60607-7061, USA, Fax: (+1) 312-355-0836Search for more papers by this author First published: 14 January 2003 https://doi.org/10.1002/anie.200390064Citations: 147 † The support of the National Science Foundation (CHE-0096889) and the National Institutes of Health (GM-64444) is gratefully acknowledged. 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 The copper-catalyzed cycloisomerization of thioalkynyl ketones 1 a and thioalkynyl imines 1 b allows the efficient synthesis of 3-thio-substituted furans 3 a and pyrroles 3 b, an important class of heterocyclic unit previously inaccessible by standard cycloisomerization techniques. A plausible mechanism for this unusual cascade involves a 1,2-migration of the thio group in the intermediate keto- and iminoallenyl sulfides 2. DMA=N,N-dimethylacetamide. Citing Literature Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2003/z19912_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. Volume42, Issue1January 3, 2003Pages 98-101 RelatedInformation