10.1002/adsc.201801324
Advanced Synthesis & Catalysis
Corrigan, S. Shanmugam, J. Xu, C. Boyer, Chem. Soc.
2013, 15, 4218; c) T. B. Nguyen, K. Pasturaud, L.
Ermolenko, A. Al-Mourabit, Org. Lett. 2015, 17, 2562;
d) X. Che, J. Jiang, F. Xiao, H. Huang, G.-J. Deng, Org.
Lett. 2017, 19, 4576; e) H. Liu, X. Jiang, Chem. Asian J.
2003, 8, 2546; f) T. B. Nguyen, Adv. Synth. Catal. 2017,
359, 1066; g) X. Wang, X. Qiu, J. Wei, J. Liu, S. Song,
W. Wang, N. Jiao, Org. Lett. 2018, 20, 2632; h) M. Wu,
Y. Jiang, Z. An, Z. Qi, R.-L. Yan, Adv. Synth. Catal.
2018, 10.1002/adsc.20180 0693; i) M. Wang, Q. Fan, X.
Jiang, Org. Lett. 2016, 18, 5756; j) Y. Hu, Z. Yin, T.
Werner, A. Spannenberg, X.-F. Wu, Eur. J. Org. Chem.
2018, 1274; k) J. Ying, H. Wang, X. Qi, J.-B. Peng, X.-
F. Wu, Eur. J. Org. Chem. 2018, 688; l) Z. Wang, Z.
Qu, F. Xiao, H. Huang, G.-J. Deng, Adv. Synth. Catal.
2018, 360, 796.
Rev. 2016, 45, 6165; c) D. C. Fabry, M. Rueping, Acc.
Chem. Res. 2016, 49, 1969; d) D. P. Hari, B. Konig,
Angew. Chem., Int. Ed. 2013, 52, 4734; e) C. K. Prier,
D. A. Rankic, D. W. MacMillan, Chem. Rev. 2013, 113,
5322; f) D. Ravelli, M. Fagnoni, A. Albini, Chem. Soc.
Rev. 2013, 42, 97; g) D. M. Schultz, T. P. Yoon,
Science, 2014, 343, 1239176.
[4] For recent reviews, see: a) S. Möhle, M. Zirbes, E.
Rodrigo, T. Gieshoff, A. Wiebe, S. R. Waldvogel,
Angew. Chem., Int. Ed. 2018, 57, 6018; b) K.-J. Jiao,
C.-Q. Zhao, P. Fang, T.-S. Mei, Tetrahedron Lett. 2017,
58, 797; c) Z.-W. Hou, Z.-Y. Mao, H.-C. Xu, Synlett
2017, 28, 1867; d) M. Yan, Y. Kawamata, P. S. Baran,
Chem. Rev. 2017, 117, 13230.
[5] a) J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, [10] a) H. Xie, J. Cai, Z. Wang, H. Huang, G.-J. Deng, Org.
369; b) Y. Segawa, T. Maekawa, K. Itami, Angew.
Chem., Int. Ed. 2015, 54, 66.
Lett. 2016, 18, 2196; b) G. Li, H. Xie, J. Chen, Y. Guo,
G.-J. Deng, Green Chem. 2017, 19, 4043.
[6] a) I. F. Perepichka, D. F. Perepichka, Handbook of [11] a) Z.-H. Ren, Z.-Y. Zhang, B.-Q. Yang, Y.-Y. Wang,
ThiophenebasedMaterials: Applications in Organic
Electronics, Photonics; Wiley-VCH: Weinheim, 2009;
b) K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki,
Adv. Mater. 2011, 23, 4347; c) W. Jiang, Y. Li, Z.
Wang, Chem. Soc. Rev. 2013, 42, 6113; d) I. Osaka, S.
Shinamura, T. Abe, K. Takimiya, J. Mater. Chem. C.
2013, 1, 1297; e) M. E. Cinar, T. Ozturk, Chem. Rev.
2015, 115, 3036; f) D. A. Boyd, Angew. Chem., Int. Ed.
2016, 55, 15486.
Z.-H. Guan, Org. Lett. 2011, 13, 5394; b) X. Tang, L.
Huang, C. Qi, W. Wu, H. Jiang, Chem. Commun. 2013,
49, 9597; c) H. Huang, X. Ji, X. Tang, M. Zhang, X. Li,
H. Jiang, Org. Lett. 2013, 15, 6254; d) Y. Wei, N.
Yoshikai, J. Am. Chem. Soc. 2013, 135, 3756; e) H.
Huang, J. Cai, X. Ji, F. Xiao, Y. Chen, G.-J. Deng,
Angew. Chem., Int. Ed. 2016, 55, 307; f) W. W. Tan, Y.
J. Ong, N. Yoshikai, Angew. Chem., Int. Ed. 2017, 56,
8240; g) C. Zhu, R. Zhu, H. Zeng, F. Chen, C. Liu, W.
Wu, H. Jiang, Angew. Chem., Int. Ed. 2017, 56, 13324.
[7] a) M. Iwao, M. L. Lee, R. N. Castle, J. Heterocycl.
Chem. 1980, 17, 1259; b) Y. Fukutomi, M. Nakano, J.- [12] a) M.-N. Zhao, Z.-H. Ren, L. Yu, Y.-Y. Wang, Z.-H.
Y. Hu, I. Osaka, K. Takimiya, J. Am. Chem. Soc. 2013,
135, 11445; c) D. S. Baranov, B. Gold, S. F. Vasilevsky,
I. V. Alabugin, J. Org. Chem. 2013, 78, 2074; d) T.
Mori, T. Nishimura, T. Yamamoto, I. Doi, E. Miyazaki,
Guan, Org. Lett. 2016, 18, 1194; b) I. Deb, N. Yoshikai,
Org. Lett. 2013, 15, 4254. c) Z. G. Zhang, J. L. Li, G. S.
Zhang, N. N. Ma, Q. F. Liu, T. X. Liu, J. Org. Chem.
2015, 80, 6875.
I. Osaka, K. Takimiya, J. Am. Chem. Soc. 2013, 135, [13] a) M.-N. Zhao, R.-R. Hui, Z.-H. Ren, Y.-Y. Wang, Z.-
13900; e) K. Takimiya, M. Nakano, M. J. Kang, E.
Miyazaki, I. Osaka, Eur. J. Org. Chem. 2013, 2013, 217;
H. Guan, Org. Lett. 2014, 16, 3082; b) Z.-H. Guan, K.
Huang, S. Yu, X. Zhang, Org. Lett. 2009, 11, 481.
f) L. Meng, T. Fujikawa, M. Kuwayama, Y. Segawa, K. [14] a) M. Kitamuraand K. Narasaka, Chem. Rec. 2002, 2,
Itami, J. Am. Chem. Soc. 2016, 138, 10351.
268; b) K. Narasaka, M. Kitamura, Eur. J. Org. Chem.
2005, 4505; c) H. Huang, X. Ji, W. Wu, H. Jiang, Chem.
Soc. Rev. 2015, 44, 1155; d) H. Huang, J. Cai, G.-J.
Deng, Org. Biomol. Chem. 2016, 14, 1519.
[8] a) F. Shibahara, R. Sugiura, E. Yamaguchi, A.
Kitagawa, T. Murai, J. Org. Chem. 2009, 74, 3566; b) T.
B. Nguyen, L. Ermolenko, A. Al-Mourabit, J. Am.
Chem. Soc. 2013, 135, 118; c) Y. Xie, J. Wu, Y. Chen, [15] a) H. Huang, J. Cai, L. Tang, Z. Wang, F. Li, G.-J.
H. Huang, G.-J. Deng, Green Chem. 2016, 18, 667; d)
Y. Xie, X. Chen, Z. Wang, H. Huang, B. Yi, G.-J. Deng,
Green Chem. 2017, 19, 4294; e) J. Tan, P. Ni, H. Huang,
G.-J. Deng, Org. Biomol. Chem. 2018, 16, 4227; f) T. B.
Deng, J. Org. Chem. 2016, 81, 1499; b) Y. Xia, J. Cai,
H. Huang, G.-J. Deng, Org. Biomol. Chem. 2018, 16,
124; c) Q. Gao, Z. Liu, Y. Wang, X. Wu, J. Zhang,, A.
Wu, Adv. Synth. Catal. 2018, 360, 1364.
Nguyen, P. Retailleau, Adv. Synth. Catal. 2017, 359, [16] H. Huang, Z. Xu, X. Ji, B. Li, G.-J. Deng, Org. Lett.
3843; g) T. B. Nguyen, L. Ermolenko, W. A. Dean, A. 2018, 20, 4917.
Al-Mourabit, Org. Lett. 2012, 14, 5948; h) T. B. [17] S. Chen, J. Liu, Y. Liu, H. Su, Y. Hong, C. K. W. Jim,
Nguyen, P. Retailleau, Org. Lett. 2017, 19, 3887; i) T.
B. Nguyen, P. Retailleau, A. Al-Mourabit, Org. Lett.
2013, 15, 5238.
R. T. K. Kwok, N. Zhao, W. Qin, J. W. Y. Lam, K. S.
Wong, B. Z. Tang, Chem. Sci. 2012, 3, 1804.
[18] For Willgerodt-Kindler reaction, see: a) C. Willgerodt,
Ber. Dtsch. Chem. Ges. 1888, 21, 534; b) E. V. Brown,
Synthesis 1975, 358; c) D. L. Priebbenow, C. Bolm,
[9] a) T. B. Nguyen, L. Ermolenko, P. Retailleau, A. Al-
Mourabit, Angew. Chem., Int. Ed. 2014, 53, 13808; b) T.
B. Nguyen, L. Ermolenko, A. Al-Mourabit, Org. Lett.
Chem. Soc. Rev. 2013, 42, 7870.
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