[1] (a) Chinchilla, R.; Nájera, C. Chem. Rev. 2014, 114, 1783.
(b) Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596.
(c) Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873.
(d) Boyarskiy, V. P.; Ryabukhin, D. S.; Bokach, N. A.; Vasilyev, A. V. Chem. Rev. 2016, 116, 5894.
(e) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.
(f) Tiwari, V. K.; Mishra, B. B.; Mishra, K. B.; Mishra, N.; Singh, A. S.; Chen, X. Chem. Rev. 2016, 116, 3086.
(g) Daniel, F.; Harvey, D. M. S. Chem. Rev. 1996, 96, 271.
(h) Krause, N.; Winter, C. Chem. Soc. Rev. 2011, 40, 1994.
(i) Hirner, J. J.; Shi, Y.; Blum, S. A. Acc. Chem. Res. 2011, 44, 603.
(j) Pina, C. D.; Falletta, E.; Rossi, M. Chem. Soc. Rev. 2012, 41, 350.
(k) Stratakis, M.; Garcia, H. Chem. Rev. 2012, 112, 4469.
(l) Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448.
(m) Liu, L.-P.; Hammond, G. B. Chem. Soc. Rev. 2012, 41, 3129.
(n) Platon, M.; Amardeil, R.; Djakovitch, L.; Hierso, J. C. Chem. Soc. Rev. 2012, 41, 3929.
(o) Shiri, M. Chem. Rev. 2012, 112, 3508.
(p) Abbiati, G.; Marinelli, F.; Rossi, E.; Arcadi, A. Isr. J. Chem. 2013, 53, 856.
(q) Cariou, K.; Ronan, B.; Mignani, S.; Fensterbank, L.; Malacria, M. Angew. Chem., Int. Ed. 2007, 46, 1881.
(r) Hashmi, A. S. K.; Graf, K.; Ackermann, M.; Rominger, F. ChemCatChem 2013, 5, 1200.
(s) Kolund?i?, F.; Murali, A.; Pérez-Galán, P.; Bauer, J. O.; Strohmann, C.; Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2014, 53, 8122.
(t) Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Angew. Chem., Int. Ed. 2015, 54, 7862.
(u) Zhu, H.; Yan, B.-Y.; Cao, Y.; Chen, Z.-Y. Chin. J. Org. Chem. 2015, 35, 509 (in Chinese).(朱辉, 严冰玉, 曹杨, 陈知远, 有机化学, 2015, 35, 509.)
(v) Wang, M.-M.; Wang, Z.-X.; Shang, M.; Dai, H.-X. Chin. J. Org. Chem. 2015, 35, 570 (in Chinese).(王明明, 王子潇, 商明, 戴辉雄, 有机化学, 2015, 35, 570.)
(w) Wu, C.-R.; Yang, Y.-P.; Shi, F. Chin. J. Org. Chem. 2015, 35, 770 (in Chinese).(吴春蕊, 杨玉坡, 史峰, 有机化学, 2015, 35, 770.)
(x) Zhou, P.; Qiu, H.-H.; Shi, J.-C. Chin. J. Org. Chem. 2016, 36, 425 (in Chinese).(周鹏, 邱会华, 施继成, 有机化学, 2016, 36, 425.)
(y) Wen, Z.-G.; Tian, C.; Borzov, M. V.; Nie, W.-L Acta Chim. Sinica 2016, 74, 498 (in Chinese).(温志国, 田冲, Borzov, M. V., 聂万丽, 化学学报, 2016, 74, 498.)
(z) Wang, J.; Cui, D.-M. Chin. J. Org. Chem. 2016, 36, 1163 (in Chinese).(王剑, 崔冬梅, 有机化学, 2016, 36, 1163.)
[2] Kobayashi, Y.; Kamisaki, H.; Yanada, K.; Yanada, R.; Takemoto, Y. Tetrahedron Lett. 2005, 46, 7549.
[3] Nakao, Y.; Idei, H.; Kanyiva, K. S.; Hiyama, T. J. Am. Chem. Soc. 2009, 131, 5070.
[4] Fujihara, T.; Katafuchi, Y.; Iwai, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2010, 132, 2094.
[5] (a) Lindhardt, A. T.; Mantel, M. L. H.; Skrydstrup, T. Angew. Chem., Int. Ed. 2008, 47, 2668.
(b) Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13178.
(c) Grushin, V. V. Chem. Rev. 1996, 96, 2011.
[6] Trost, B. M.; Lumb, J. P.; Azzarelli, J. M. J. Am. Chem. Soc. 2011, 133, 740.
[7] Trost, B. M.; Taft, B. R.; Masters, J. T.; Lumb, J. P. J. Am. Chem. Soc. 2011, 133, 8502.
[8] Xu, H.-D.; Zhang, R.-W.; Li, X.; Huang, S.; Tang, W.; Hu, W.-H. Org. Lett. 2013, 15, 840.
[9] Liu, G.; Kong, W.; Che, J.-W.; Zhu, G.-G. Adv. Synth. Catal. 2014, 356, 3314.
[10] Babu, M. H.; Dwivedi, V.; Kant, R.; Reddy, M. S. Angew. Chem., Int. Ed. 2015, 54, 3783.
[11] For more examples of hydroalkynylation of alkynes, see:
(a) Katayama, H.; Yari, H.; Tanaka, M.; Ozawa, F. Chem. Commun. 2005, 4336.
(b) Bassetti, M.; Pasquini, C.; Raneri, A.; Rosato, D. J. Org. Chem. 2007, 72, 4558.
(c) Jahier, C.; Zatolochnaya, O. V.; N. Zvyagintsev, V. V.; Ananikov, P.; Gevorgyan, V. Org. Lett. 2012, 14, 2846.
(d) Chen, T.; Guo, C.; Goto, M.; Han, L.-B. Chem. Commun. 2013, 49, 7498.
(e) Xu, C.; Du, W.; Zeng, Y.; Dai, B.; Guo, H. Org. Lett. 2014, 16, 948.
(f) Platel, R. H.; Schafer, L. L. Chem. Commun. 2012, 48, 10609.
(g) Midya, G. C.; Parasar, B.; Dhara, K.; Dash, J. Org. Biomol. Chem. 2014, 12, 1812.
(h) Ventre, S.; Derat, E.; Amatore, M.; Aubert, C.; Petit, M. Adv. Synth. Catal. 2013, 355, 2584.
(i) Shen, R.-W.; Chen, K.; Deng, Q.-L.; Yang, J.-J.; Zhang, L.-X. Org. Lett. 2014, 16, 1208.
[12] Suginome, M.; Yamamoto, A.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 6358.
[13] Suginome, M.; Yamamoto, A.; Murakami, M. Angew. Chem., Int. Ed. 2005, 44, 2380.
[14] (a) Harwood, H. J. Jr.; Barbacci-Tobin, E. G.; Petras, S. F.; Lindsey, S.; Pellarin, L. D. Biochem. Pharmacol. 1997, 53, 839.
(b) Morand, P.; Bagli, J. F.; Kraml, M.; Dubuc, J. J. Med. Chem. 1964, 7, 504.
[15] Suginome, M.; Shirakura, M.; Yamamoto, A. J. Am. Chem. Soc. 2006, 128, 14438.
[16] Shimada, T.; Nakamura, I.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 10546.
[17] Nakamura, I.; Sato, Y.; Konta, S.; Terada, M. Tetrahedron Lett. 2009, 50, 2075.
[18] Wu, C.-Y.; Hu, M.; Liu, Y.; Song, R.-J.; Lei, Y.; Tang, B.-X.; Li, R.-J.; Li, J.-H. Chem. Commun. 2012, 48, 3197.
[19] Zhao, F.; Zhang, D.-Y.; Nian, Y.; Zhang, L.; Yang, W.; Liu, H. Org. Lett. 2014, 16, 5124.
[20] Wu, C.-L.; Zhao, F.; Shu, S.-J.; Wang, J.; Liu, H. RSC Adv. 2015, 5, 90396.
[21] Wu, C.-L.; Zhao, F.; Du, Y.-L.; Zhao, L.; Chen, L.; Wang, J.; Liu, H. RSC Adv. 2016, 6, 70682.
[22] Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 1940.
[23] Majumdar, K. C.; Hazra, S.; Roy, B. Tetrahedron Lett. 2011, 52, 6697.
[24] Heugebaert, T. S.; Stevens, C. V. Org. Lett. 2009, 11, 5018.
[25] Nakamura, I.; Mizushima, Y.; Yamagishi, U.; Yamamoto, Y. Tetrahedron 2007, 63, 8670.
[26] Zeng, X.-M.; Kinjo, R.; Donnadieu, B.; Bertrand, G. Angew. Chem., Int. Ed. 2010, 49, 942.
[27] Filatova, E. A.; Pozharskii, A. F.; Gulevskaya, A. V.; Ozeryanskii, V. A. J. Org. Chem. 2015, 80, 872.
[28] For more examples of addition of C-N bond to alkynes, see: (a) Nakamura, I.; Yamagishi, U.; Song, D.; Konta, S.; Yamamoto, Y. Chem. Asian J. 2008, 3, 285.
(b) Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250.
(c) Cacchi, S.; Fabrizi, G.; Pace, Paola. J. Org. Chem. 1998, 63, 1001.
(d) Li, G.-T.; Huang, X.-G.; Zhang, L.-M. Angew. Chem., Int. Ed. 2008, 47, 346.
[29] Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett. 1998, 39, 5101.
[30] Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022.
[31] Fürstner, A.; Davies, P. W. J. Am. Chem. Soc. 2005, 127, 15024.
[32] Liang, Z.-Q.; Ma, S.-M.; Yu, J.-H.; Xu, R.-R. J. Org. Chem. 2007, 72, 9219.
[33] Dubé, P.; Toste, F. D. J. Am. Chem. Soc. 2006, 128, 12062.
[34] Nakamura, I.; Chan, C. S.; Araki, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 309.
[35] (a) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260.
(b) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627.
(c) Harrak, Y.; Blaszykowski, C.; Bernard, M.; Cariou, K.; Mainetti, E.; Mourie`s, V.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. J. Am. Chem. Soc. 2004, 126, 8656.
(d) Kusama, H.; Miyashita, Y.; Takaya, J.; Iwasawa, N. Org. Lett. 2006, 8, 289.
[36] Nakamura, I.; Chan, C. S.; Araki, T.; Terada, M. Yamamoto, Y. Adv. Synth. Catal. 2009, 351, 1089.
[37] Komeyama, K.; Takahashi, K.; Takaki, K. Org. Lett. 2008, 10, 5119.
[38] Shi, Y.; Roth, K. E.; Ramgren, S. D.; Blum, S. A. J. Am. Chem. Soc. 2009, 131, 18022.
[39] Ueda, M.; Sato, A.; Ikeda, Y.; Miyoshi, T.; Naito, T.; Miyata, O. Org. Lett. 2010, 12, 2594.
[40] Watanabe, K.; Mino, T.; Ikematsu, T.; Hatta, C.; Yoshida, Y.; Sakamoto, M. Org. Chem. Front. 2016, 3, 979.
[41] For more examples of addition of C-O bond to alkynes, see: (a) Ackermann, M.; Bucher, J.; Rappold, M.; Graf, K.; Rominger, F.; Hashmi, A. S. Chem. Asian J. 2013, 8, 1786.
(b) Hashmi, A. S. K.; Lothschütz, C.; Döpp, R.; Ackermann, M.; Becker, J. D. B.; Rudolph, M.; Scholz, C.; Rominger, F. Adv. Synth. Catal. 2012, 354, 133.
(c) Monteiro, N.; Balme, G. Synlett 1998, 746.
(d) Fürstner, A.; Heilmann, E. K.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 4760.
(e) Tsuda, T.; Ohashi, Y.; Nagahama, N.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 2650.
(f) Obata, T.; Suzuki, S.; Nakagawa, A.; Kajihara, R.; Noguchi, K.; Saito, A. Org. Lett. 2016, 18, 4136.
[42] Yeon, S. Ho.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159.
[43] Asao, N.; Yoshikawa, E.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4874.
[44] Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781.
[45] Asao, N.; Tomeba, H.; Yamamoto, Y. Tetrahedron Lett. 2005, 46, 27.
[46] Asao, N.; Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3797.
[47] Asao, N.; Shimada, T.; Shimada, T.; Yamamoto, Y. J. Am. Chem. Soc. 2001, 123, 10899.
[48] Matsuda, T.; Kadowaki, S.; Yamaguchi, Y.; Murakami, M. Chem. Commun. 2008, 2744.
[49] Matsuda, T.; Yamaguchi, Y.; Shigeno, M.; Sato, S.; Murakami, M. Chem. Commun. 2011, 47, 8697.
[50] Zhou, T.; Xia, Y.-Z. Organometallics 2014, 33, 4230.
[51] Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1998, 120, 5339.
[52] Nakamura, I.; Bajracharya, G. B.; Wu, H.; Oishi, K.; Mizushima, Y.; Gridnev, I. D.; Yamamoto, Y. J. Am. Chem. Soc. 2004, 126, 15423.
[53] Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 2649.
[54] Toyofuku, M.; Fujiwara, S.; Shinike, T.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2005, 127, 9706.
[55] Kamiya, I.; Kawakami, J.; Yano, S.; Nomoto, A.; Ogawa, A. Organometallics. 2006, 25, 3562.
[56] Nakamura, I.; Sato, T.; Yamamoto, Y. Angew. Chem., Int. Ed. 2006, 45, 4473.
[57] Hooper, J. F.; Chaplin, A. B.; González-Rodríguez, C.; Thompson, A. L.; Weller, A. S.; Willis, M. C. J. Am. Chem. Soc. 2012, 134, 2906.
[58] For more examples of addition of C-S bond to alkynes, see:
(a) Lee, Y. T.; Choi, S. Y.; Chung, Y. K. Tetrahedron Lett. 2007, 48, 5673.
(b) Davies, P. W.; Albrecht, S. J. C. Chem. Commun. 2008, 238.
[59] Li, Y.-B.; Liu, X.-H.; Jiang, H.-F.; Feng, Z.-N. Angew. Chem., Int. Ed. 2010, 49, 3338.
[60] Murai, M.; Hatano, Ryo.; Kitabata, S.; Ohe, K. Chem. Commun. 2011, 47, 2375.
[61] Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
[62] Kashiwabara, T.; Fuse, K.; Hua, R.; Tanaka, M. Org. Lett. 2008, 10, 5469.
[63] Fielding, M. R.; Grigg, R.; Urchb, C. J. Chem. Commun. 2000, 2239.
[64] Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2009, 131, 6668.
[65] Le, C. M.; Menzies, P. J. C.; Petrone, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2015, 54, 254.
[66] (a) Legault, C. Y.; Garcia, Y.; Merlic, C. A.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 12664.
(b) Xue, L.; Lin, Z. Chem. Soc. Rev. 2010, 39, 1692.
(c) García-Melchor, M.; Braga, A. A. C.; Lledós, A.; Ujaque, G.; Maseras, F. Acc. Chem. Res. 2013, 46, 2626.
[67] Liu, Z.-Q.; Wang, J.-G.; Zhao, Y.-K.; Zhou, B. Adv. Synth. Catal. 2009, 351, 371.
[68] Xu, T.; Hu, X. Angew. Chem., Int. Ed. 2015, 54, 1307.
[69] Che, C.; Zheng, H.-L; Zhu, G.-G. Org. Lett. 2015, 17, 1617.
[70] Chen, X.-Y.; Kong, W.; Cai, H.-T.; Kong, L.-C.; Zhu, G.-G. Chem. Commun. 2011, 47, 2164.
[71] Cai, H.-T.; Yuan, Z.-L.; Zhu, W.-D.; Zhu, G.-G. Chem. Commun. 2011, 47, 8682.
[72] Belhomme, M.; Dru, D.; Xiong, H.; Cahard, D.; Besset, T.; Poisson, T.; Pannecoucke, X. Synthesis 2014, 46, 1859.
[73] Xu, T.; Cheung, C. W.; Hu, X. Angew. Chem., Int. Ed. 2014, 53, 4910.
[74] For more examples of addition of C-X (X=Cl, Br, I) bonds to alkynes, see: (a) Ichinose, Y.; Matsunaga, S.-I.; Fugami, K.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1989, 30, 3155.
(b) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257.
(c) Tang, Y.; Li, C.-Z. Org. Lett. 2004, 6, 3229.
(d) Kippo, T.; Fukuyama, T.; Ryu, I. Org. Lett. 2010, 12, 4006.
(e) Li, J.-X.; Yang, S.-R.; Wu, W.-Q.; Qi, C.-R.; Deng, Z.-X.; Jiang, H.-F. Tetrahedron 2014, 70, 1516.
(f). Yeh, M.-C. P.; Lin, H.-H.; Kuo, S.-F.; Chen, P.-J.; Hong, J.-W. Adv. Synth. Catal. 2014, 356, 3816.
(g) Wallentin, C.-J.; Nguyen, J. D.; Finkbeiner, P.; Stephenson, C. R. J. J. Am. Chem. Soc. 2012, 134, 8875.
(h) Arceo, E.; Montroni, E.; Melchiorre, P. Angew. Chem., Int. Ed. 2014, 53, 120648.
(i) Iwai, T.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc. 2012, 134, 1268.
(j) Goossen, L. J.; Rodríguez. N.; Goossen, K. Angew. Chem., Int. Ed. 2009, 48, 9592.
[75] Fukuyama, Y.; Nakahara, M.; Minami, H.; Kodama, M. Chem. Pharm. Bull. 1996, 44, 1418.
[76] Sakai, A.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1999, 40, 4211.
[77] Sasai, A.; Aoyama, T.; Shioiri, T. Heterocycles 2000, 52, 643. |