Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and N‐(ortho‐Chloromethyl)aryl Amides

Angewandte Chemie International EditionVolume 51, Issue 36 p. 9137-9140 Communication Synthesis of Indoles through Highly Efficient Cascade Reactions of Sulfur Ylides and N-(ortho-Chloromethyl)aryl Amides† Qing-Qing Yang, Qing-Qing Yang Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorCong Xiao, Cong Xiao College of Chemistry, Peking University, Beijing 100871 (China)Search for more papers by this authorDr. Liang-Qiu Lu, Dr. Liang-Qiu Lu Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorJing An, Jing AnSearch for more papers by this authorFen Tan, Fen Tan Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorBin-Jie Li, Bin-Jie Li Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorProf. Dr. Wen-Jing Xiao, Corresponding Author Prof. Dr. Wen-Jing Xiao [email protected] Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China) State Key Laboratory of Applied Organic Chemistry, Lanzhou Universitry, Lanzhou 730000 (China)Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this author Qing-Qing Yang, Qing-Qing Yang Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorCong Xiao, Cong Xiao College of Chemistry, Peking University, Beijing 100871 (China)Search for more papers by this authorDr. Liang-Qiu Lu, Dr. Liang-Qiu Lu Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorJing An, Jing AnSearch for more papers by this authorFen Tan, Fen Tan Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorBin-Jie Li, Bin-Jie Li Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this authorProf. Dr. Wen-Jing Xiao, Corresponding Author Prof. Dr. Wen-Jing Xiao [email protected] Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China) State Key Laboratory of Applied Organic Chemistry, Lanzhou Universitry, Lanzhou 730000 (China)Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079 (China)Search for more papers by this author First published: 06 August 2012 https://doi.org/10.1002/anie.201203657Citations: 129 † We are grateful to the National Science Foundation of China (nos. 21072069 and 21002036) and the National Basic Research Program of China (2011CB808603) for support of this research. 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 Batting the ylides: A simple procedure carried out under mild conditions allows the direct and efficient synthesis of structurally diverse indoles. This approach involves a cascade reaction of sulfur ylides and N-(ortho-chloromethyl)aryl amides (see scheme). 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_201203657_sm_miscellaneous_information.pdf1.8 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. References 1 1aJ. E. Saxton, Nat. Prod. Rep. 1997, 14, 559; 1bM. Toyota, N. Ihara, Nat. Prod. Rep. 1998, 15, 327, and references therein; 1cJ. A. Joule, Product Class 13: Indole and Its Derivatives, Thieme, Stuttgart, 2001; 1dT. Kawasaki, K. Higuchi, Nat. Prod. Rep. 2005, 22, 761; for a recent review, see 1eM. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786; Angew. Chem. Int. Ed. 2009, 48, 9608. 2For selected reviews on indole syntheses, see 2aT. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 2001, 2491; 2bL. Ackermann, Synlett 2007, 507; 2cK. Krüger, A. Tillack, M. Beller, Adv. Synth. Catal. 2008, 350, 2153; 2dS. Cacchi, G. Fabrizi, A. Goggiamani, Org. Biomol. Chem. 2011, 9, 641; 2eS. Cacchi, G. Fabrizi, Chem. Rev. 2006, 106, 2875. 3 3aE. Fischer, F. Jourdan, Ber. Dtsch. Chem. Ges. 1883, 16, 2241; 3bE. Fischer, O. Hess, Ber. Dtsch. Chem. Ges. 1884, 17, 559. 4For representative examples, see 4aJ. Bonjoch, J. Catena, N. Valls, J. Org. Chem. 1996, 61, 7106; 4bR. Iyengar, K. Schildknegt, J. Aube, Org. Lett. 2000, 2, 1625; 4cC. W. Roberson, K. A. Woerpel, J. Am. Chem. Soc. 2002, 124, 11342; 4dT. Gan, R. Liu, P. Yu, S. Zhao, J. M. Cook, J. Org. Chem. 1997, 62, 9298; 4eH. Ueda, H. Satoh, K. Matsumoto, K. Sugimoto, T. Fukuyama, H. Tokuyama, Angew. Chem. 2009, 121, 7736; Angew. Chem. Int. Ed. 2009, 48, 7600; 4fS. Müller, M. J. Webber, B. List, J. Am. Chem. Soc. 2011, 133, 18534. 5For representative examples, see 5aT. Lipin'ska, Chem. Heterocycl. Compd. 2001, 37, 231; 5bC.-Y. Chen, C. H. Senanayake, T. J. Bill, R. D. Larsen, T. R. Verhoeven, P. J. Reider, J. Org. Chem. 1994, 59, 3738; 5cA. R. Katritzky, S. Rachwal, S. Bayyuk, Org. Prep. Proced. Int. 1991, 23, 357; 5dM. Inman, C. J. Moody, Chem. Commun. 2011, 47, 788; 5eB. Narayana, B. V. Ashalatha, R. K. K. Vijaya, J. Fernandes, B. K. Sarojini, Bioorg. Med. Chem. 2005, 13, 4638; 5fM. Inman, A. Carbone, C. J. Moody, J. Org. Chem. 2012, 77, 1217; 5gB. A. Haag, Z.-G. Zhang, J.-S. Li, P. Knochel, Angew. Chem. 2010, 122, 9703; Angew. Chem. Int. Ed. 2010, 49, 9513. 6For selected examples, see 6aR. C. Larock, E. K. Yum, J. Am. Chem. Soc. 1991, 113, 6689; 6bJ. Barluenga, M. Trincado, E. Rubio, J. González, Angew. Chem. 2003, 115, 2508; Angew. Chem. Int. Ed. 2003, 42, 2406; 6cB. Witulski, C. Alayrac, L. Tevzadze-saeftel, Angew. Chem. 2003, 115, 4392; Angew. Chem. Int. Ed. 2003, 42, 4257; 6dM. Nazaré, C. Schneider, A. Lindenschmidt, D. W. Will, Angew. Chem. 2004, 116, 4626; Angew. Chem. Int. Ed. 2004, 43, 4526; 6eA. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, L. M. Parisi, J. Org. Chem. 2005, 70, 6213; 6fB. M. Trost, A. McClory, Angew. Chem. 2007, 119, 2120; Angew. Chem. Int. Ed. 2007, 46, 2074; 6gK. Cariou, B. Ronan, S. Mignani, L. Fensterbank, M. Malacria, Angew. Chem. 2007, 119, 1913; Angew. Chem. Int. Ed. 2007, 46, 1881; 6hI. Nakamura, U. Yamagishi, D. Song, S. Konta, Y. Yamamoto, Angew. Chem. 2007, 119, 2334; Angew. Chem. Int. Ed. 2007, 46, 2284; 6iG. T. Li, X. G. Huang, L. M. Zhang, Angew. Chem. 2008, 120, 352; Angew. Chem. Int. Ed. 2008, 47, 346. 7For selected examples, see 7aC. Crotti, S. Cenini, B. Rindone, S. Tollari, F. Demartin, J. Chem. Soc. Chem. Commun. 1986, 784; 7bM. Akazome, T. Kondo, Y. Watanabe, J. Org. Chem. 1994, 59, 3375; 7cB. C. G. Söderberg, S. R. Banini, M. R. Tunner, A. R. A. Minter, K. Arrington, Synthesis 2008, 903; 7dJ. L. Rutherford, M. P. Rainka, S. L. Buchwald, J. Am. Chem. Soc. 2002, 124, 15168; 7eA. Wong, J. T. Kuethe, I. W. Davies, D. L. Hughes, J. Org. Chem. 2004, 69, 7761; 7fK. Okuro, J. Gurnham, H. Alper, J. Org. Chem. 2011, 76, 4715. 8For selected examples, see 8aB. J. Stokes, H.-J. Dong, B. E. Leslie, A. L. Pumphrey, T. G. Driver, J. Am. Chem. Soc. 2007, 129, 7500; 8bM. Shen, B. E. Leslie, T. G. Driver, Angew. Chem. 2008, 120, 5134; Angew. Chem. Int. Ed. 2008, 47, 5056; 8cJ.-J. Li, T.-S. Mei, J.-Q. Yu, Angew. Chem. 2008, 120, 6552; Angew. Chem. Int. Ed. 2008, 47, 6452; 8dS. Würtz, S. Rakshit, J. J. Neumann, T. Dröge, F. Glorius, Angew. Chem. 2008, 120, 7340; Angew. Chem. Int. Ed. 2008, 47, 7230; 8eD. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474; 8fZ.-Z. Shi, C. Zhang, S. Li, D.-L. Pan, S.-T. Ding, Y.-X. Cui, N. Jiao, Angew. Chem. 2009, 121, 4642; Angew. Chem. Int. Ed. 2009, 48, 4572; 8gR. Bernini, G. Fabrizi, A. Sferrazza, S. Cacchi, Angew. Chem. 2009, 121, 8222; Angew. Chem. Int. Ed. 2009, 48, 8078; 8hD. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326; 8iY.-C. Tan, J. F. Hartwig, J. Am. Chem. Soc. 2010, 132, 3676. 9For selected examples, see: 9aC. M. Coleman, D. F. O'Shea, J. Am. Chem. Soc. 2003, 125, 4054; 9bJ. R. Dunetz, R. L. Danheiser, J. Am. Chem. Soc. 2005, 127, 5776; 9cA. Saito, A. Kanno, Y. Hanzawa, Angew. Chem. 2007, 119, 4005; Angew. Chem. Int. Ed. 2007, 46, 3931; 9dJ. Barluenga, A. Jiménez-Aquino, C. Valdés, F. Aznar, Angew. Chem. 2007, 119, 1551; Angew. Chem. Int. Ed. 2007, 46, 1529; 9eO. Leogane, H. Lebel, Angew. Chem. 2008, 120, 356; Angew. Chem. Int. Ed. 2008, 47, 350; 9fS.-L. Cui, J. Wang, Y.-G. Wang, J. Am. Chem. Soc. 2008, 130, 13526; 9gT. Jensen, H. Pedersen, B. Bang-Andersen, R. Madsen, M. Jørgensen, Angew. Chem. 2008, 120, 902; Angew. Chem. Int. Ed. 2008, 47, 888; 9hN. Okamoto, Y. Miwa, H. Minami, K. Takeda, R. Yanada, Angew. Chem. 2009, 121, 9873; Angew. Chem. Int. Ed. 2009, 48, 9693; 9iJ. Barluenga, A. Aquino, F. Aznar, C. Valdes, J. Am. Chem. Soc. 2009, 131, 4031; 9jY.-Z. Wang, L.-W. Ye, L.-M. Zhang, Chem. Commun. 2011, 47, 7815; 9kB. J. Stokes, S. Liu, T. G. Driver, J. Am. Chem. Soc. 2011, 133, 4702; 9lK. Sun, S. Liu, P. M. Bec, T. G. Driver, Angew. Chem. 2011, 123, 1740; Angew. Chem. Int. Ed. 2011, 50, 1702. 10E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 1965, 87, 1353. 11For selected reviews, see 11aB. M. Trost, L. S. Melvin, Sulfur Ylides, Academic Press, New York, 1976; 11bA.-H. Li, L.-X. Dai, V. K. Aggarwal, Chem. Rev. 1997, 97, 2341; 11cV. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611; 11dE. M. McGarrigle, E. L. Myers, O. Illaa, M. A. Shaw, S. L. Riches, V. K. Aggarwal, Chem. Rev. 2007, 107, 5841; 11eX.-L. Sun, Y. Tang, Acc. Chem. Res. 2008, 41, 937. 12For selected examples, see 12aV. K. Aggarwal, H. Abdel-Rahman, R. V. H. Jones, H. Y. Lee, B. D. Reid, J. Am. Chem. Soc. 1994, 116, 5973; 12bV. K. Aggarwal, J. G. Ford, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Am. Chem. Soc. 1996, 118, 7004; 12cV. K. Aggarwal, H. Abdel-Rahman, L. Fan, R. V. H. Jones, M. C. H. Standen, Chem. Eur. J. 1996, 2, 1024; 12dV. K. Aggarwal, J. G. Ford, S. Fonquerna, H. Adams, R. V. H. Jones, R. Fieldhouse, J. Am. Chem. Soc. 1998, 120, 8328; 12eV. K. Aggarwal, E. Alonso, I. Bae, G. Hynd, K. M. Lydon, M. J. Palmer, M. Patel, M. Porcelloni, J. Richardson, R. A. Stenson, J. R. Studley, J.-L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2003, 125, 10926; 12fV. K. Aggarwal, I. Bae, H.-Y. Lee, J. Richardson, D. T. Williams, Angew. Chem. 2003, 115, 3396; Angew. Chem. Int. Ed. 2003, 42, 3274; 12gV. K. Aggarwal, J. Charmant, L. Dudin, M. Porcelloni, J. Richardson, Proc. Natl. Acad. Sci. USA 2004, 101, 5467; 12hG. Y. Fang, O. A. Wallner, N. D. Blasio, X. Ginesta, J. N. Harvey, V. K. Aggarwal, J. Am. Chem. Soc. 2007, 129, 14632. 13For selected examples, see 13aL.-W. Ye, X.-L. Sun, C.-Y. Zhu, Y. Tang, Org. Lett. 2006, 8, 3853; 13bL.-W. Ye, X.-L. Sun, C.-Y. Li, Y. Tang, J. Org. Chem. 2007, 72, 1335; 13cQ.-G. Wang, X.-M. Deng, B.-H. Zhu, L.-W. Ye, X.-L. Sun, C.-Y. Li, C.-Y. Zhu, Q. Shen, Y. Tang, J. Am. Chem. Soc. 2008, 130, 5408; 13dJ.-C. Zheng, C.-Y. Zhu, X.-L. Sun, Y. Tang, L.-X. Dai, J. Org. Chem. 2008, 73, 6909. 14For selected examples, see 14aL.-Q. Lu, Y.-J. Cao, X.-P. Liu, J. An, C.-J. Yao, Z.-H. Ming, W.-J. Xiao, J. Am. Chem. Soc. 2008, 130, 6946; 14bL.-Q. Lu, F. Li, J. An, J.-J. Zhang, X.-L. An, Q.-L. Hua, W.-J. Xiao, Angew. Chem. 2009, 121, 9706; Angew. Chem. Int. Ed. 2009, 48, 9542; 14cL.-Q. Lu, J.-J. Zhang, F. Li, J. An, Q.-L. Hua, J.-R. Chen, W.-J. Xiao, Angew. Chem. 2010, 122, 4597; Angew. Chem. Int. Ed. 2010, 49, 4495; 14dL.-Q. Lu, F. Li, J. An, Y. Cheng, J.-R. Chen, W.-J. Xiao, Chem. Eur. J. 2012, 18, 4073. 15For selected examples, see 15aJ. L. Loebach, D. M. Bennett, R. L. Danheiser, J. Am. Chem. Soc. 1998, 120, 9690; 15bH.-J. Gais, L. R. Reddy, G. S. Babu, G. Raabe, J. Am. Chem. Soc. 2004, 126, 4859; 15cJ. M. Schomaker, V. R. Pulgam, B. Borhan, J. Am. Chem. Soc. 2004, 126, 13600; 15dM. F. Oswald, S. A. Raw, R. J. K. Taylor, Chem. Commun. 2005, 2253; 15eT. Sone, G. Lu, S. Matsunaga, M. Shibasaki, Angew. Chem. 2009, 121, 1705; Angew. Chem. Int. Ed. 2009, 48, 1677; 15fZ.-L. Chen, J.-L. Zhang, Chem. Asian J. 2009, 4, 1527; 15gS. Kramer, T. Skrydstrup, Angew. Chem. 2012, 124, 4759; Angew. Chem. Int. Ed. 2012, 51, 4681; 15hJ.-R. Chen, W.-R. Dong, M. Candy, F.-F. Pan, M. Jörres, C. Bolm, J. Am. Chem. Soc. 2012, 134, 6924. 16L.-Q. Lu, J.-R. Chen, W.-J. Xiao, Acc. Chem. Res. 2012, DOI: . 17aM. Komiya, S. Asano, N. Koike, E. Koga, J. Igarashi, S. Nakatani, Y. Isobe, Bioorg. Med. Chem. Lett. 2011, 21, 1456; 17bS. Mahboobi, H. Pongratz, H. Hufsky, J. Hockemeyer, M. Frieser, A. Lyssenko, D. H. Paper, J. Bürgermeister, F. Böhmer, H. Fiebig, A. M. Burger, S. Baasner, T. Beckers, J. Med. Chem. 2001, 44, 4535. 18aH.-X. Wu, F. Xue, X. Xiao, Y. Qin, J. Am. Chem. Soc. 2010, 132, 14052; 18bH.-G. Lehmann, Tetrahedron Lett. 1968, 9, 607; 18cF. J. Robertson, B. D. Kenimer, J. Wu, Tetrahedron 2011, 67, 4327; 18dH. Steinhagen, E. J. Corey, Angew. Chem. 1999, 111, 2054; Angew. Chem. Int. Ed. 1999, 38, 1928; 18eL. Petit, M. G. Banwell, A. C. Willis, Org. Lett. 2011, 13, 5800. 19For some mechanism studies, see the Supporting Information. Citing Literature Volume51, Issue36September 3, 2012Pages 9137-9140 ReferencesRelatedInformation