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A New Access to 4 H ‐Quinolizines from 2‐Vinylpyridine and Alkynes Promoted by Rhodium–N‐Heterocyclic‐Carbene Catalysts

2013; Wiley; Volume: 19; Issue: 12 Linguagem: Inglês

10.1002/chem.201300236

1521-3765

Ramón Azpíroz, Andrea Di Giuseppe, Ricardo Castarlenas, Jesús J. Pérez‐Torrente, Luis A. Oro,

Cyclopropane Reaction Mechanisms

Chemistry – A European JournalVolume 19, Issue 12 p. 3812-3816 Communication A New Access to 4 H-Quinolizines from 2-Vinylpyridine and Alkynes Promoted by Rhodium–N-Heterocyclic-Carbene Catalysts Ramón Azpíroz, Ramón Azpíroz Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorDr. Andrea Di Giuseppe, Dr. Andrea Di Giuseppe Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorDr. Ricardo Castarlenas, Corresponding Author Dr. Ricardo Castarlenas rcastar@unizar.es Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain) ARAID Foundation ResearcherDepartamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorProf. Jesús J. Pérez-Torrente, Prof. Jesús J. Pérez-Torrente Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorProf. Luis A. Oro, Corresponding Author Prof. Luis A. Oro oro@unizar.es Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this author Ramón Azpíroz, Ramón Azpíroz Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorDr. Andrea Di Giuseppe, Dr. Andrea Di Giuseppe Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorDr. Ricardo Castarlenas, Corresponding Author Dr. Ricardo Castarlenas rcastar@unizar.es Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain) ARAID Foundation ResearcherDepartamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorProf. Jesús J. Pérez-Torrente, Prof. Jesús J. Pérez-Torrente Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this authorProf. Luis A. Oro, Corresponding Author Prof. Luis A. Oro oro@unizar.es Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Departamento Química Inorgánica, Instituto Síntesis Química y Catálisis Homogénea, Universidad de Zaragoza-CSIC, Pl. S. Francisco S/N 50009 Zaragoza (Spain)Search for more papers by this author First published: 21 February 2013 https://doi.org/10.1002/chem.201300236Citations: 30 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 Forging the lock that autolocks! RhNHC catalysts promote a new access to 4 H-quinolizine species from 2-vinylpyridine and terminal and internal alkynes through CH activation and CC coupling reactions (see figure). N-Bridgehead heterocycle formation is favored for internal- over terminal-substituted butadienylpyridine derivatives in a thermal 6π-electrocyclization process. Citing Literature Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description chem_201300236_sm_miscellaneous_information.pdf3.4 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. Volume19, Issue12March 18, 2013Pages 3812-3816 RelatedInformation