TfOH/Fe(OTf)3 Cocatalyzed Reaction of Arylallenes with Alcohols for Structurally Diverse Indene Derivatives
Corresponding Author
Congrong Liu
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu, 211167 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
E-mail: [email protected]Search for more papers by this authorHaiyun Zhang
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu, 211167 China
Search for more papers by this authorLianghui Ding
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu, 211167 China
Search for more papers by this authorJuan Liu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorCorresponding Author
Congrong Liu
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu, 211167 China
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
E-mail: [email protected]Search for more papers by this authorHaiyun Zhang
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu, 211167 China
Search for more papers by this authorLianghui Ding
School of Environment Engineering, Nanjing Institute of Technology, 1 Hongjingdadao, Nanjing, Jiangsu, 211167 China
Search for more papers by this authorJuan Liu
Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
Search for more papers by this authorAbstract
The indene moiety is an important unit because of its presence in many chemical catalysts, functional materials and biologically relevant molecules. Herein, we report a facile reaction of arylallenes with benzylic or allylic alcohols through TfOH/Fe(OTf)3 cocatalyzed cleavage of sp3 carbon-oxygen. In the presence of 5 mol% TfOH and 5 mol% Fe(OTf)3, a range of arylallenes undergo carbocation initiated cyclization reaction with alkyl alcohols to give structurally diverse polysubstituted indenes in good to excellent yields. H2O is the sole byproduct that makes this transformation highly atom-economic and environmentally benign.
Supporting Information
| Filename | Description |
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| cjoc201800099-sup-0001-SuppInfo.pdfPDF document, 1.8 MB | Supporting Information |
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References
- 1(a) Clegg, N. J.; Paruthiyil, S.; Leitman, D. C.; Scanlan, T. S. J. Med. Chem. 2005, 48, 5989; (b) Korte, A.; Legros, J.; Bolm, C. Synlett 2004, 2397; (c) Maguire, A. R.; Papot, S.; Ford, A.; Touhey, S.; O'Connor, R.; Clynes, M. Synlett 2001, 41; (d) Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. Rev. 1999, 99, 723; (e) Senanayake, C. H.; Roberts, F. E.; Michele, L. M.; Ryan, K. M.; Liu, J.; Fredenburgh, L. E.; Foster, B. S.; Douglas, A. W.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1995, 36, 3993; (f) Shanmugam, P.; Rajasingh, P. Chem. Lett. 2005, 34, 1494.
- 2(a) Wang, B. Coord. Chem. Rev. 2006, 250, 242; (b) Alt, H. G.; Koppl, A. Chem. Rev. 2000, 100, 1205.
- 3(a) Barbera, J.; Rakitin, O. A.; Ros, M. B.; Torroba, T. Angew. Chem. Int. Ed. 1998, 37, 296;
10.1002/(SICI)1521-3773(19980216)37:3<296::AID-ANIE296>3.0.CO;2-U CAS PubMed Web of Science® Google Scholar(b) Yang, J.; Lakshmikantham, M. V.; Cava, M. P.; Lorcy, D.; Bethelot, J. R. J. Org. Chem. 2000, 65, 6739.
- 4(a) Alexander, P.; Antonio, M.; Nuno, M. Chem. Eur. J. 2016, 22, 14471; (b) Yang, C.; Xu, Z. L.; Shao, H.; Mou, X. Q.; Wang, J.; Wang, S. H. Org. Lett. 2015, 17, 5288; (c) Dethe, D. H.; Murhade, G. M.; Ghosh, S. J. Org. Chem. 2015, 80, 8367; (d) Ding, W.; Shi, X. L. Chin. J. Chem. 2015, 33, 1276; (e) Dethe, D. H.; Murhade, G. Org. Lett. 2013, 15, 429; (f) Muthusamy, S.; Sivaguru, M. Org. Lett. 2014, 16, 4248; (g) Huang, X. C.; Yang, X. H.; Song, R. J.; Li, J. H. J. Org. Chem. 2014, 79, 1025; (h) Wang, Y.; Liao, W.; Huang, G. P.; Xia, Y. Z.; Yu, Z. X. J. Org. Chem. 2014, 79, 5684; (i) Huguet, N.; Lebœuf, D.; Echavarren, A. M. Chem. Eur. J. 2013, 19, 6581; (j) Hou, Q. W.; Zhang, Z. H.; Kong, F. J.; Wang, S. Z.; Wang, H. Q.; Yao, Z.-J. Chem. Commun. 2013, 49, 695; (k) Meng, B.; Ma, S. Org. Lett. 2012, 14, 2674; (l) Usanov, D. L.; Yamamoto, H. Org. Lett. 2012, 14, 414; (m) Liu, C.-R.; Wang, T.-T. Qi, Q.-B.; Tian, S.-K. Chem. Commun. 2012, 48, 10913; (n) Qiu, G. S.; Ding, Q. P.; Gao, K.; Peng, Y. Y. J. Comb. Sci. 2011, 13, 13; (o) Patureau, F. W.; Besset, T.; Kuhl, N.; Glorius, F. J. Am. Chem. Soc. 2011, 133, 2154; (p) Zhu, Y.; Yin, G.; Hong, D.; Lu, P.; Wang, Y. Org. Lett. 2011, 13, 1024; (q) Panteleev, J.; Huang, R. Y.; Lui, E. K. J.; Lautens, M. Org. Lett., 2011, 13, 5314; (r) Zeng, X.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 17638; (s) Kurouchi, H.; Sugimoto, H.; Otani, Y.; Ohwada, T. J. Am. Chem. Soc. 2010, 132, 807; (t) Liu, C.-R.; Yang, F.-L.; Jin, Y.-Z.; Ma, X.-T.; Cheng, D.-J.; Li, N.; Tian, S.-K. Org. Lett., 2010, 12, 3832; (u) Fuchibe, K.; Atobe, K.; Fujita, Y.; Mori, K.; Akiyama, T. Chem. Lett. 2010, 867; (v) Chatterjee, P. N.; Roy, S. J. Org. Chem. 2010, 75, 4413; (w) Ye, S.; Ren, H., Wu, J. J. Comb. Chem. 2010, 12, 670; (x) Yamazaki, Y.; Yamamoto, Y.; Fukushima, M.; Takebayashi, T.; Mikata, Y. J. Org. Chem. 2010, 75, 5216.
- 5(a) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12; (b) Ma, S. Acc. Chem. Res. 2003, 36, 701; (c) Sydnes, L. K. Chem. Rev. 2003, 103, 1133; (d) Brandsma, L.; Nedolya, N. A. Synthesis 2004, 735; (e) Tius, M. A. Acc. Chem. Res. 2003, 36, 284; (f) Wei, L. L.; Xiong, H.; Hsung, R. P. Acc. Chem. Res. 2003, 36, 773; (g) Ma, S. Chem. Rev. 2005, 105, 2829; (h) Ma, S. Aldrichim. Acta 2007, 40, 91; (i) Kim, H.; Williams, L. J. Curr. Opin. Drug Disc. Dev. 2008, 11, 870; (j) Brasholz, M.; Reissig, H.-U.; Zimmer, R. Acc. Chem. Res. 2009, 42, 45; (k) Ma, S. Acc. Chem. Res. 2009, 42, 1679; (l) Wang, Z. J.; Benitez, D.; Tkatchouk, E.; Goodward, W. A.; Toste, F. D. J. Am. Chem. Soc. 2010, 132, 13064; (m) Martin, T. J.; Vakhshori, V. G.; Tran, Y. S.; Kwon, O. Org. Lett. 2011, 13, 2586; (n) Muneoz, M. P. Org. Biomol. Chem. 2012, 10, 3584; (o) Andrews, I. P.; Blank, B. R.; Kwon, O. Chem. Commun. 2012, 48, 5373; (p) Meng, W.; Zhao, H.-T.; Nie, J.; Zheng, Y.; Fu, A. P.; Ma, J.-A. Chem. Sci. 2012, 3, 3053; (q) Fang, Y-Q.; Tadross, P. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2014, 136, 17966; (r) Hurtado-Rodrigo, C.; Hoehne, S.; Munoz, M. Chem. Commun. 2014, 50, 1494; (s) Bang, J. Y.; Kim, H.; Yu, M. O. Org. Lett. 2015, 17, 1573; (t) Kidonakis, M.; Stratakis, M. Org. Lett. 2015, 17, 4538; (u) Liu, J.; Liu, Q.; Franke, B.; Jackstell, R.; Beller, M. J. Am. Chem. Soc. 2015, 137, 8556; (v) Lin, W. L.; Cheng, J. J.; Ma, S. Adv. Synth. Catal. 2016, 358, 1989; (w) Khrakovsky, D. A.; Tao, C. Z.; Johnson, M. W.; Thornbury, R. T.; Shevick, S. L.; Toste. F. D. Angew. Chem. Int. Ed. 2016, 55, 6079; (x) Eshon, J.; Landis, C. R.; Schomaker, J. M. J. Org. Chem. 2017, 82, 9270; (y) Martzel, T.; Lohier, J.; Gaumont, A. C.; Perrio, S. Adv. Synth. Catal. 2017, 360, 231.
- 6(a) Krause, N.; Hashmi, A. S. K. Modern Allene Chemistry, VCH, Weinheim, 2004, pp. 50—102; (b) Jana, U.; Biswas, S.; Maiti, S. Eur. J. Org. Chem. 2008, 5798.
- 7For the details of experimental procedure see supporting informant.
- 8(a) Kuang, J.-Q.; Ma, S.-M. J. Am. Chem. Soc. 2010, 132, 1786; (b) Xiao, Q.; Xia, Y.; Li, H.; Zhan, Y.; Wang, J.-B. Angew. Chem. Int. Ed. 2011, 50, 1114.
- 9 Liu, C.-R.; Wang, T.-T.; Qi, Q.-B.; Tian, S.-K. Chem. Commun. 2012, 48, 10913.
- 10 Mellni, M. J. Chem. Res., Synop. 1979, 342.
