Role of Copper in the Stereoselective Metal-Promoted Cyclotrimerisation of Polycyclic Alkenes
2002; Wiley; Volume: 2002; Issue: 23 Linguagem: Inglês
10.1002/1099-0690(200212)2002
ISSN1434-193X
AutoresPaola Peluso, Ottorino De Lucchi, Sergio Cossu,
Tópico(s)Catalysis for Biomass Conversion
ResumoEuropean Journal of Organic ChemistryVolume 2002, Issue 23 p. 4032-4036 Full Paper Role of Copper in the Stereoselective Metal-Promoted Cyclotrimerisation of Polycyclic Alkenes Paola Peluso, Paola Peluso Dipartimento di Chimica, Università Ca' Foscari di Venezia, Calle Larga Santa Marta 2137, 30123 Venezia, Italy, Fax: (internat.) + 39-041/234-8517Search for more papers by this authorOttorino De Lucchi, Ottorino De Lucchi Dipartimento di Chimica, Università Ca' Foscari di Venezia, Calle Larga Santa Marta 2137, 30123 Venezia, Italy, Fax: (internat.) + 39-041/234-8517Search for more papers by this authorSergio Cossu, Sergio Cossu [email protected] Dipartimento di Chimica, Università Ca' Foscari di Venezia, Calle Larga Santa Marta 2137, 30123 Venezia, Italy, Fax: (internat.) + 39-041/234-8517Search for more papers by this author Paola Peluso, Paola Peluso Dipartimento di Chimica, Università Ca' Foscari di Venezia, Calle Larga Santa Marta 2137, 30123 Venezia, Italy, Fax: (internat.) + 39-041/234-8517Search for more papers by this authorOttorino De Lucchi, Ottorino De Lucchi Dipartimento di Chimica, Università Ca' Foscari di Venezia, Calle Larga Santa Marta 2137, 30123 Venezia, Italy, Fax: (internat.) + 39-041/234-8517Search for more papers by this authorSergio Cossu, Sergio Cossu [email protected] Dipartimento di Chimica, Università Ca' Foscari di Venezia, Calle Larga Santa Marta 2137, 30123 Venezia, Italy, Fax: (internat.) + 39-041/234-8517Search for more papers by this author First published: 12 November 2002 https://doi.org/10.1002/1099-0690(200212)2002:23 3.0.CO;2-XCitations: 5Read 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 onEmailFacebookTwitterLinkedInRedditWechat Abstract Copper-mediated stereoselective cyclotrimerisation of polycyclic alkenes is reported. The mechanism involved provides strong support for the involvement of a CuIII intermediate in cross-coupling reactions of sp2-carbon atoms. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002) Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2046/2002/o02324_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. References 1 1a F.-G. Klärner , U. Burkert , M. Kamieth , R. Boese , J. Benet-Bucholz , Chem. Eur. J. 1999 , 5 , 1700 −1707 . 10.1002/(SICI)1521-3765(19990604)5:6 3.0.CO;2-9 CASWeb of Science®Google Scholar 1b C. Zonta , S. Cossu , O. De Lucchi , Eur. J. Org. Chem. 2000 , 1965 −1971 . 10.1002/(SICI)1099-0690(200005)2000:10 3.0.CO;2-C CASWeb of Science®Google Scholar 2 2a N. L. Franck , K. K. Baldridge , J. S. Siegel , J. Am. Chem. Soc. 1995 , 117 , 2102 −2103 . 10.1021/ja00112a028 Web of Science®Google Scholar 2b I. Alkorta , I. Rozas , J. Elguero , Tetrahedron 2001 , 57 , 6043 −6049 . 10.1016/S0040-4020(01)00585-3 CASWeb of Science®Google Scholar 2c F.-G. Klärner , Angew. Chem. Int. Ed. 2001 , 40 , 3977 −3981 . 10.1002/1521-3773(20011105)40:21 3.0.CO;2-N CASPubMedWeb of Science®Google Scholar 3 3a J.-F. Nierengarten , L. Oswald , J.-C. Eckert , J.-F. Nicoud , N. Armaroli , Tetrahedron Lett. 1999 , 40 , 5681 −5684 . 10.1016/S0040-4039(99)01060-6 CASWeb of Science®Google Scholar 3b P. E. Georghiou , S. Mizyed , S. Chowdhury , Tetrahedron Lett. 1999 , 40 , 611 −614 . 10.1016/S0040-4039(98)02447-2 CASWeb of Science®Google Scholar 4 4a D. Felder , B. Heinrich , D. Guillon , J.-F. Nicoud , J.-F. Nierengarten , Chem. Eur. J. 2000 , 6 , 3501 −3507 . 10.1002/1521-3765(20001002)6:19 3.0.CO;2-0 CASPubMedWeb of Science®Google Scholar 4b G. Cooke , N. Kaushal , N. Boden , R. J. Bushby , Z. Lu , O. Lozman , Tetrahedron Lett. 2000 , 41 , 7955 −7959 . 10.1016/S0040-4039(00)01370-8 CASWeb of Science®Google Scholar 4c S. J. Holder , J. A. A. Elemans , J. J. J. M. Donners , M. J. Boeraskker , R. de Gelder , J. Barberà , A. E. Rowan , R. J. M. Nolte , J. Org. Chem. 2001 , 66 , 391 −399 . 10.1021/jo0008035 CASPubMedWeb of Science®Google Scholar 5 5a S. Cossu , O. De Lucchi , A. Paulon , P. Peluso , C. Zonta , Tetrahedron Lett. 2001 , 42 , 3515 −3518 . 10.1016/S0040-4039(01)00495-6 CASWeb of Science®Google Scholar 5b S. Cossu , C. Cimenti , P. Peluso , A. Paulon , O. De Lucchi , Angew. Chem. Int. Ed. 2001 , 40 , 4086 −4089 . 10.1002/1521-3773(20011105)40:21 3.0.CO;2-5 CASPubMedWeb of Science®Google Scholar 6 6a P. Gassman , I. Gennick , J. Am. Chem. Soc. 1980 , 102 , 6863 −6964 . 10.1021/ja00542a041 CASWeb of Science®Google Scholar 6b S.B. Singh , H. Hart , J. Org. Chem. 1990 , 55 , 3412 −3415 . 10.1021/jo00297a086 CASWeb of Science®Google Scholar 6c K. Komatsu , S. Aonuma , Y. Jinbu , R. Tsuji , C. Hirosawa , K. Takeuchi , J. Org. Chem. 1991 , 56 , 195 −203 . 10.1021/jo00001a039 CASWeb of Science®Google Scholar 6d R. Durr , S. Cossu , V. Lucchini , O. De Lucchi , Angew. Chem. Int. Ed. Engl. 1997 , 36 , 2805 −2807 . 10.1002/anie.199728051 CASWeb of Science®Google Scholar 7 L. A. Paquette , C. M. Moorhoff , G. D. Maynard , E. R. Hickey , R. D. Rogers , J. Org. Chem. 1991 , 56 , 2449 −2455 . 10.1021/jo00007a036 CASWeb of Science®Google Scholar 8 C. Zonta , S. Cossu , P. Peluso , O. De Lucchi , Tetrahedron Lett. 1999 , 40 , 8185 −8188 . 10.1016/S0040-4039(99)01736-0 CASWeb of Science®Google Scholar 9 9a R. F. Heck , Org. React. 1982 , 27 , 345 −390 . CASWeb of Science®Google Scholar 9b A. De Meijere , F. E. Meyer , Angew. Chem. Int. Ed. Engl. 1994 , 33 , 2379 −2411 . 10.1002/anie.199423791 Web of Science®Google Scholar 9c G. T. Crisp , Chem. Soc. Rev. 1998 , 27 , 427 −436 and references cited therein. 10.1039/a827427z CASWeb of Science®Google Scholar 9d I. P. Beletskaya , A. V. Cheprakov , Chem. Rev. 2000 , 100 , 3009 −3066 . 10.1021/cr9903048 CASPubMedWeb of Science®Google Scholar 10 10a E. Nakamura , S. Mori , M. Nakamura , K. Morokuma , J. Am. Chem. Soc. 1997 , 119 , 4887 . 10.1021/ja964208p CASWeb of Science®Google Scholar 10b E. Nakamura , S. Mori , K. Morokuma , J. Am. Chem. Soc. 1998 , 120 , 8273 −8274 . 10.1021/ja9800030 CASWeb of Science®Google Scholar 10c E. Nakamura , M. Yamanaka , J. Am. Chem. Soc. 1999 , 121 , 8941 −8942 . 10.1021/ja991324u CASWeb of Science®Google Scholar 10d E. Nakamura , S. Mori , Angew. Chem. Int. Ed. 2000 , 39 , 3750 −3771 . 10.1002/1521-3773(20001103)39:21 3.0.CO;2-L CASPubMedWeb of Science®Google Scholar 10e G. H. Posner, Org. React. 1972, 19, 1−113. Google Scholar 10f A. S. E. Karlström , J.-E. Bäckvall , Chem. Eur. J. 2001 , 7 , 1981 −1989 . 10.1002/1521-3765(20010504)7:9 3.0.CO;2-C CASPubMedWeb of Science®Google Scholar 11 G. D. Allred , L. S. Liebeskind , J. Am. Chem. Soc. 1996 , 118 , 2748 −2749 . 10.1021/ja9541239 CASWeb of Science®Google Scholar 12 E. Piers , M. A. Romero , J. Am. Chem. Soc. 1996 , 118 , 1215 −1216 . 10.1021/ja953648y CASWeb of Science®Google Scholar 13 Experiments carried out on 2,3-bis(trimethylstannyl)benzonorbornadiene resulted only in complex mixtures of unstable dimeric compounds. This appears to be an important result, because according to the postulated mechanism it underlines the key role of the bromine as an essential co-participant promoter for the oxidative addition of a third monomeric unit. Google Scholar 14 14a As reported by: S. Mori , E. Nakamura , Tetrahedron Lett. 1999 , 40 , 5319 −5322 for angles smaller than ca. 150°, the HOMO of a dialkylcuprate should have good interactions with the π*-orbital of an acetylene or an olefin. Such an interaction should create a typical case of Dewer−Chatt−Ducanson d-π* back-donation, which should compensate for the energy loss due to bending. For earlier discussions on d-orbital participation in the cuprate/olefin interaction see: 10.1016/S0040-4039(99)00966-1 CASWeb of Science®Google Scholar 14b E. J. Corey , N. W. Boaz , Tetrahedron Lett. 1984 , 25 , 3063 −3066 . 10.1016/0040-4039(84)80008-8 CASWeb of Science®Google Scholar 15 The mesomeric and inductive features of the substituent (Br or SnR3) on each monomer, makes the bond between the metal centre and the trialkylstannyl-substituted monomer stronger than otherwise, because of the possibility of more efficient back-donation in the presence of stannylated substituents that, possessing low-energy d-orbitals, may exert a stabilising effect. Google Scholar 16 T. N. Mitchell , K. Bottcher , P. Blekmann , B. Costisella , C. Schwittek , C. Nettelbeck , Eur. J. Org. Chem. 1999 , 2413 −2417 . 10.1002/(SICI)1099-0690(199909)1999:9 3.0.CO;2-0 CASWeb of Science®Google Scholar Citing Literature Volume2002, Issue23December 2002Pages 4032-4036 ReferencesRelatedInformation
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