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Controllable [2+2] Cycloadditions of 1,5‐Bisallenyl‐Substituted Compounds

2006; Wiley; Volume: 45; Issue: 47 Linguagem: Inglês

10.1002/anie.200602847

ISSN

1521-3773

Autores

Xuefeng Jiang, Xin Cheng, Shengming Ma,

Tópico(s)

Synthetic Organic Chemistry Methods

Resumo

Angewandte Chemie International EditionVolume 45, Issue 47 p. 8009-8013 Communication Controllable [2+2] Cycloadditions of 1,5-Bisallenyl-Substituted Compounds† Xuefeng Jiang, Xuefeng Jiang State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-7510Search for more papers by this authorXin Cheng, Xin Cheng State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-7510Search for more papers by this authorShengming Ma Prof. Dr., Shengming Ma Prof. Dr. [email protected] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-7510Search for more papers by this author Xuefeng Jiang, Xuefeng Jiang State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-7510Search for more papers by this authorXin Cheng, Xin Cheng State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-7510Search for more papers by this authorShengming Ma Prof. Dr., Shengming Ma Prof. Dr. [email protected] State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P.R. China, Fax: (+86) 21-6416-7510Search for more papers by this author First published: 27 November 2006 https://doi.org/10.1002/anie.200602847Citations: 84 † Financial support from the National Natural Science Foundation of China (20121202, 20423001, and 20332060) and the Shanghai Municipal Committee of Science and Technology are greatly appreciated. We thank Z. Liang in our research group for reproducing the reactions of 6 j in Table 1 and 6 c in Table 3. 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 onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract Come on allenes: [2+2] Cycloadditions of 1,5-bisallenyl compounds were realized in controllable head-to-head and tail-to-tail manners, resulting in the formation of [3.2.0] and [5.2.0] bicyclic compounds, respectively (see scheme). The bicyclic compounds include double bonds suitable for further elaboration and thus these reactions may be powerful tools in organic synthesis. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2006/z602847_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 1aJ. E. 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Commun. 2005, 5670; for theoretical studies of these reactions, see: B. Engels, M. Hanrath, J. Am. Chem. Soc. 1998, 120, 6356; P. G. Wenthold, M. A. Lipton, J. Am. Chem. Soc. 2000, 122, 9265; P. W. Musch, B. Engels, J. Am. Chem. Soc. 2001, 123, 5557. 7 7aL. Skattebøl, S. Solomon, J. Am. Chem. Soc. 1965, 87, 4506; 7bK. M. Nicholas, J. Am. Chem. Soc. 1975, 97, 3255; 7cP. J. Garratt, S. B. Neoh, J. Org. Chem. 1979, 44, 2667; 7dF. Toda, K. Tdnaka, I. Sano, T. Isozaki, Angew. Chem. 1994, 106, 1856; Angew. Chem. Int. Ed. Engl. 1994, 33, 1757; 7eT. Shimizu, K. Sakamaki, N. Kamigata, Tetrahedron Lett. 1997, 38, 8529; 7fT. Shimizu, K. Sakamaki, D. Miyasaka, N. Kamigata, J. Org. Chem. 2000, 65, 1721; 7gS. Saito, K. Hirayama, C. Kabuto, Y. Yamamoto, J. Am. Chem. Soc. 2000, 122, 10776; for the Pd-catalyzed formation of four-membered products from an intramolecular coupling reaction starting from bisallenes and Bu3SnH or Bu3SnMBu3 (M=Sn or Ge), see: 7hS.-K. Kang, T.-G. Baik, A. N. Kulak, Y.-H. Ha, Y. Lim, J. Park, J. Am. Chem. Soc. 2000, 122, 11529; 7iY.-T. Hong, S.-K. Yoon, S.-K. Kang, C.-M. Yu, Eur. J. Org. Chem. 2004, 4628. 8For benzoannulation of 1,4-bisallenes, see: P. Aubert, B. Princet, J. Pornet, Synth. Commun. 1997, 27, 2615; S. Kitagaki, Y. Okumura, C. Mukai, Tetrahedron Lett. 2006, 47, 1849. 9S. Ma, P. Lu, L. Lu, H. Hou, J. Wei, Q. He, Z. Gu, X. Jiang, X. Jin, Angew. Chem. 2005, 117, 5409; Angew. Chem. Int. Ed. 2005, 44, 5275. 10Crystal data for compound 7 e: C22H22O4S2, Mr=414.52, monoclinic, space group P2(1)/c, a=13.4605(12), b=9.1336(8), c=16.4267(15) Å, α=90, β=93.632(2), γ=90°, V=2015.5(3) Å3, T=293(2) K, Z=4, final R indices [I>2σ(I)], R1=0.0525, wR2=0.1323, R indices (all data), R1=0.0726, wR2=0.1402, , reflections collected/unique: 11 518/4362 (Rint=0.0572). 11 11aJ. Tsuji, Transition Metal Reagents and Catalysts, Wiley, Chichester, 2000; 11b Handbook of Organopalladium Chemistry for Organic Synthesis (Ed.: ), Wiley-Interscience, 2002; J. 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Chem. Soc. Dalton Trans. 1973, 2491; 12hD. J. Pasto, N.-Z. Huang, C. W. Eigenbrot, J. Am. Chem. Soc. 1985, 107, 3160; 12iD. J. Pasto, N.-Z. Huang, C. W. Eigenbrot, Organometallics 1985, 4, 1386; 12jK. Takagi, I. Tomita, T. Endo, Macromolecules 1998, 31, 6741, and references therein; 12kG. Ingrosso, M. Iqbal, R. Rossi, L. Porri, Chim. Ind. 1973, 55, 540; 12lM. Iyoda, S. Tanaka, M. Nose, M. Oda, J. Chem. Soc. Chem. Commun. 1983, 1058; M. Iyoda, S. Tanaka, H. Otani, M. Nose, M. Oda, J. Am. Chem. Soc. 1988, 110, 8494; M. Iyoda, Y. Kuwatani, M. Oda, J. Am. Chem. Soc. 1989, 111, 3761; 12mK. C. Chao, D. K. Rayabarapu, C.-C. Wang, C.-H. Cheng, J. Org. Chem. 2001, 66, 8804. 13A. Togni, L. M. Venanzi, Angew. Chem. 1994, 106, 517; Angew. Chem. Int. Ed. Engl. 1994, 33, 497; . 14Crystal data for compound 8 a: C15H17NO2S, Mr=275.36, monoclinic, space group P2(1)/n, a=8.2755(12), b=10.8834(17), c=16.437(2) Å, α=90, β=101.394(3), γ=90°, V=1451.3(4) Å3, T=293(2) K, Z=4, final R indices [I>2σ(I)], R1=0.0455, wR2=0.0731, R indices (all data), R1=0.1847, wR2=0.0991, reflections collected/unique: 8406/3162 (Rint=0.0989). 15Crystal data for compound 9 na: C24H28N2O4, Mr=408.48, monoclinic, space group P2(1), a=10.7399 (18), b=5.7808 (9), c=17.346(3) Å, α=90, β=97.128(3), γ=90°, V=1068.6(3) Å3, T=293 (2) K, Z=2, final R indices [I>2σ(I)], R1=0.0543, wR2=0.1196, R indices (all data), R1=0.0675, wR2=0.1245, reflections collected/unique: 6334/2563 (R(int)=0.1458). CCDC-291779 (7 e), CCDC-291780 (8 a), CCDC-60887 (9 na) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif. 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