Zhang et al.
COMMUNICATION
ca 2015, 73, 705; (q) Tang, M.; Wu, Y.; Liu, Y.; Cai, M.; Xia, F.;
Liu, S.; Hu, W. Acta Chim. Sinica 2016, 74, 54.
References
[1] For selected reviews, see: (a) Baumgartner, T.; Réau, R. Chem. Rev.
2006, 106, 4681; (b) He, X.; Baumgartner, T. RSC Adv. 2013, 3,
11334; (c) Takimiya, K.; Osaka, I.; Mori, T.; Nakano, M. Acc. Chem.
Res. 2014, 47, 1493; (d) Narita, A.; Wang, X.-Y.; Feng, X.; Müllen,
K. Chem. Soc. Rev. 2015, 44, 6616.
[2] For selected reviews, see: (a) Guldi, D.; Illescas, B. M.; Atienza, C.
M.; Wielopolskia, M.; Martín, N. Chem. Soc. Rev. 2009, 38, 1587; (b)
Nierengarten, I.; Nierengarten, J.-F. Chem. Asian J. 2014, 9, 1436;
(c) Lebedeva, M. A.; Chamberlain, T. W.; Khlobystov, A. N. Chem.
Rev. 2015, 115, 11301; (d) Lu, J.; Yang, J.; Carvalho, A.; Liu, H.; Lu,
Y.; Sow, C. H. Acc. Chem. Res. 2016, 49, 1806.
[3] For selected examples, see: (a) Wilkinson, G.; Rosenblum, M.;
Whiting, M. C.; Woodward, R. B. J. Am. Chem. Soc. 1952, 74, 2125;
(b) Long, N. J.; Kowalski, K. Ferrocenes: Ligands, Materials and
Biomolecules, Eds: Štěpnička, P., Chichester, UK., 2008; (c) Werner,
H. Angew. Chem., Int. Ed. 2012, 51, 6052; (d) Wang, L.; Liu, M.;
Meng, Y.; Li, H.; Zhang, Y.; Yao, S. Chin. J. Chem. 2013, 31, 845; (e)
Ye, X.; Zheng, Y.; Wang, X. Chin. J. Chem. 2014, 32, 498; (f)
Adelhardt, M.; Sutter, J.; Seppelt, K.; Malischewski, M.; Meyer, K.
Science 2016, 353, 678.
[4] For selected reviews, see: (a) Mueller-Westerhoff, U. T. Angew.
Chem., Int. Ed. 1986, 25, 702; (b) Staveren, D. R.; Metzler-Nolte, N.
Chem. Rev. 2004, 104, 5931; (c) Atkinson, R. C. J.; Gibson, V. C.;
Long, N. J. Chem. Soc. Rev. 2004, 33, 313; (d) Albada, B.; Metz-
ler-Nolte, N. Chem. Rev. 2016, 116, 11797.
[5] For selected reviews, see: (a) Boorman, T. C.; Larrosa, I. Chem. Soc.
Rev. 2011, 40, 1910; (b) Zhao, J.; Zhang, Q. Acta Chim. Sinica 2015,
73, 1235; (c) Dorel, R.; Echavarren, A. M. Chem. Rev. 2015, 115,
9028; (d) Li, Y.; Li, W.; Zhang, J. Chem. Eur. J. 2016, 22, DOI:
10.1002/chem.201602822; (e) Zi, W.; Toste, F. D. Chem. Soc. Rev.
2016, 45, 4567; (f) Boyarskiy, V. P.; Ryabukhin, D. S.; Bokach, N.
A.; Vasilyev, A. V. Chem. Rev. 2016, 116, 5894; (g) Aguilar, E.; Sanz,
R.; Fernandez-Rodríguez, M. A.; García-García, P. Chem. Rev. 2016,
116, 8256; For selected examples, see: (h) Fürstner, A.; Mamane, V.
J. Org. Chem. 2002, 67, 6264; (i) Fürstner, A.; Mamane, V. Chem.
Commun. 2003, 2112; (j) Mamane, V.; Hannen, P.; Fürstner, A.
Chem. Eur. J. 2004, 10, 4556; (k) Fürstner, A.; Kennedy, J. W. J.
Chem. Eur. J. 2006, 12, 7398; (l) Carreras, J.; Patil, M.; Thiel, W.;
Alcarazo, M. J. Am. Chem. Soc. 2012, 134, 16753; (m) Yamamoto,
K.; Okazumi, M.; Suemune, H.; Usui, K. Org. Lett. 2013, 15, 1806;
(n) Oyama, H.; Nakano, K.; Harada, T.; Kuroda, R.; Naito, M.; No-
busawa, K.; Nozaki, K. Org. Lett. 2013, 15, 2104; (o) Carreras, J.;
Gopakumar, G.; Gu, L.; Gimeno, A.; Linowski, P.; Petuskova, J.;
Thiel, W.; Alcarazo, M. J. Am. Chem. Soc. 2013, 135, 18815; (p)
Zheng, J.-F.; Xie, Z.-Q.; Chen, X.-J.; Huang, P.-Q. Acta Chim. Sini-
[6] (a) Gao, D. W.; Yin, Q.; Gu, Q.; You, S. L. J. Am. Chem. Soc. 2014,
136, 4841; (b) Deng, R.; Huang, Y.; Ma, X.; Li, G.; Zhu, R.; Wang,
B.; Kang, Y. B.; Gu, Z. J. Am. Chem. Soc. 2014, 136, 4472; (c) Liu,
L.; Zhang, A. A.; Zhao, R. J.; Li, F.; Meng, T. J.; Ishida, N.; Mura-
kami, M.; Zhao, W. X. Org. Lett. 2014, 16, 5336; (d) Ma, X.; Gu, Z.
RSC Adv. 2014, 4, 36241; (e) Gao, D.-W.; Zheng, C.; Gu, Q.; You,
S.-L. Organometallics 2015, 34, 4618; (f) Liu, S.; Ma, W.; Zheng,
Z.; Ma, Z.; Cao, D. Chin. J. Org. Chem. 2015, 35, 228; (g) Li, L.;
Zhou, B.; Ye, L. Chin. J. Org. Chem. 2015, 35, 655; (h) Wang, Y.;
Zhang, A.; Liu, L.; Kang, J.; Zhang, F.; Ma, W. Chin. J. Org. Chem.
2015, 35, 1399; (i) Zhang, X.; Sun, X.; Zhang, H.; Cui, X.; Ma, M.
Chin. J. Org. Chem. 2015, 35, 1469.
[7] (a) Urbano, A.; Hernandez-Torres, G.; del Hoyo, A. M.; Mar-
tínez-Carrión, A.; Carmen Carreño, M. Chem. Commun. 2016, 52,
6419; (b) Shibata, T.; Uno, N.; Sasaki, T.; Kanyiva, K. S. J. Org.
Chem. 2016, 81, 6266.
[8] Our work on gold-catalyzed cyclization reaction: (a) Zhang, M.;
Zhang, J. Chem. Commun. 2012, 48, 6399; (b) Qian, D.; Zhang, J.
Chem. Commun. 2012, 48, 7082; (c) Qian, D.; Hu, H.; Liu, F.; Tang,
B.; Ye, W.; Wang, Y.; Zhang, J. Angew. Chem., Int. Ed. 2014, 53,
13751; (d) Liu, F.; Wang, Y.; Ye, W.; Zhang, J. Org. Chem. Front.
2015, 2, 221; (e) Wang, Y.; Zhang, P.; Liu, Y.; Xia, F.; Zhang, J.
Chem. Sci. 2015, 6, 5564; (f) Wang, Y.; Zhang, P.; Qian, D.; Zhang, J.
Angew. Chem., Int. Ed. 2015, 54, 14849; (g) Zhang, Y.; Xiao, Y.;
Zhang, J. Synthesis 2016, 48, 512; (h) Hu, H.; Wang, Y.; Qian, D.;
Zhang, Z.-M.; Liu, L.; Zhang, J. Org. Chem. Front. 2016, 3, 759; (i)
Ma, B.; Wu, Z.; Huang, B.; Liu, L.; Zhang, J. Chem. Commun. 2016,
52, 9351.
[9] Synthesis of 5 via Negishi coupling: Zhang, Q.-W.; An, K.; Liu,
L.-C.; Yue, Y.; He, W. Angew. Chem., Int. Ed. 2015, 54, 6918.
[10] For reviews of Sonogashira coupling, see: (a) Chinchilla, R.; Nájera,
C. Chem. Rev. 2007, 107, 874; (b) Doucet, H.; Hierso, J.-C. Angew.
Chem., Int. Ed. 2007, 46, 834; (c) Chinchilla, R.; Nájera, C. Chem.
Soc. Rev. 2011, 40, 5084; (d) Seechurn, C. C. C. J.; Kitching, M. O.;
Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062.
[11] A highly efficient and practical Sonogashira coupling has been ap-
plied for the first time to prepare various substituted
1-ferrocenyl-2-(non-terminalethynyl)benzene 1.
[12] The gold catalyst is also known to serve as the σ acid to form the
gold acetylid through silicon gold transmetalation. For some reports
in silicon gold transmatalation, see: (a) Zhang, S.; Xu, Z.; Jia, J.;
Tungab, C.-H.; Xu, Z. Chem. Commun. 2014, 50, 12084; (b)
Falivene, L.; Nelson, D. J.; Dupuy, S.; Nolan, S. P.; Poater, A.;
Cavallo, L. Chemistry Open 2016, 5, 60.
(Lu, Y.)
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Chin. J. Chem. 2017, XX, 1—4