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M. Noikham et al.
Paper
Synthesis
Acknowledgment
Chem. Soc. Rev. 2012, 41, 3464. (d) Huang, X.-F.; Salman, M.;
Huang, Z.-Z. Chem. Eur. J. 2014, 20, 6618. (e) Wang, R.; Li, Y.; Jin,
R.-X.; Wang, X.-S. Chem. Sci. 2017, 8, 3838.
We thank the Department of Chemistry and the Central Instrument
Facility (CIF) at Faculty of Science, Mahidol University for providing
research facilities, and Science Achievement Scholarship of Thailand
(SAST) for supporting student scholarships to M.N. and T.K.
(7) For selected examples, see: (a) Shirakawa, E.; Uchiyama, N.;
Hayashi, T. J. Org. Chem. 2011, 76, 25. (b) Brzozowski, M.; Forni,
J. A.; Savage, G. P.; Polyzos, A. Chem. Commun. 2015, 51, 334.
(c) Liu, L.-W.; Wang, Z.-Z.; Zhang, H.-H.; Wang, W.-S.; Zhang, J.-
Z.; Tang, Y. Chem. Commun. 2015, 51, 9531. (d) Su, H.; Wang, L.;
Rao, H.; Xu, H. Org. Lett. 2017, 19, 2226.
Supporting Information
(8) For selected reviews on synthetic use of molecular iodine, see:
(a) Kupper, F. C.; Feiters, M. C.; Olofsson, B.; Kaiho, T.; Yanagida,
S.; Zimmermann, M. B.; Carpenter, L. J.; Luther, G. W. III.; Lu, Z.;
Jonsson, M.; Kloo, L. Angew. Chem. Int. Ed. 2011, 50, 11598.
(b) Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 45, 979.
(c) Ren, Y.-M.; Cai, C.; Yang, R.-C. RSC Adv. 2013, 3, 7182. (d) Wu,
X.-F.; Gong, J.-L.; Qi, X. Org. Biomol. Chem. 2014, 12, 5807.
(e) Yusubov, M. S.; Zhdankin, V. V. Resource-Efficient Technol.
2015, 1, 49. (f) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016,
116, 3328. (g) Kohlhepp, S. V.; Gulder, T. Chem. Soc. Rev. 2016,
45, 6270.
(9) For selected examples, see: (a) Wan, C.; Gao, L.; Wang, Q.;
Zhang, J.; Wang, Z. Org. Lett. 2010, 12, 3902. (b) Wang, Q.; Wan,
C.; Gu, Y.; Zhang, J.; Gao, L.; Wang, Z. Green Chem. 2011, 13, 578.
(c) Yan, Y.; Wang, Z. Chem. Commun. 2011, 47, 9513. (d) Tian, J.-
S.; Ng, K. W. J.; Wong, J.-R.; Loh, T.-P. Angew. Chem. Int. Ed. 2012,
51, 9105. (e) Liu, D.; Lei, A. Chem. Asian J. 2015, 10, 806. (f) Wu,
X.; Geng, X.; Zhao, P.; Wu, Y.-D.; Wu, A.-X. Org. Lett. 2017, 19,
4584.
(10) (a) Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th ed.; Blackwell
Science: Oxford, 2000. (b) Akins, P. T.; Atkinson, R. P. Curr. Med.
Res. Opin. 2002, 18, 9. (c) Mamedov, V. A.; Zhukova, N. A. Prog.
Heterocycl. Chem. 2013, 25, 1.
(11) For reviews, see: (a) Rangisetty, J. B.; Gupta, C. N. V. H. B.;
Prasad, A. L.; Srinivas, P.; Sridhar, N.; Parimoo, P.;
Veeranjaneyulu, A. J. Pharm. Pharmacol. 2001, 53, 1409.
(b) Carta, A.; Piras, S.; Loriga, G.; Paglietti, G. Mini-Rev. Med.
Chem. 2006, 6, 1179. (c) Li, X.; Yang, K.-H.; Li, W.-L.; Xu, W.-F.
Drugs Future 2006, 31, 979. (d) Chen, D.; Bao, W. Adv. Synth.
Catal. 2010, 352, 955. (e) Jeon, S. O.; Lee, J. Y. J. Mater. Chem.
2012, 22, 7239. (f) Quinn, J.; Guo, C.; Ko, L.; Sun, B.; He, Y.; Li, Y.
RSC Adv. 2016, 6, 22043.
(12) (a) Heldin, C. H.; Westermark, B. Cell Regul. 1990, 1, 555.
(b) Myers, M. R.; He, W.; Hanney, B.; Setzer, N.; Maguire, M. P.;
Zulli, A.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Spada, A.
P. Bioorg. Med. Chem. Lett. 2003, 13, 3091. (c) He, W.; Myers, M.
R.; Hanney, B.; Spada, A. P.; Bilder, G.; Galzcinski, H.; Amin, D.;
Needle, S.; Page, K.; Jayyosi, Z.; Perrone, M. H. Bioorg. Med.
Chem. Lett. 2003, 13, 3097. (d) Gazit, A.; Yee, K.; Uecker, A.;
Bohmer, F. D.; Sjoblom, T.; Ostman, A.; Waltenberger, J.;
Golomb, G.; Banai, S.; Heinrich, M. C.; Levitzki, A. Bioorg. Med.
Chem. 2003, 11, 2007. (e) Nixey, T.; Tempest, P.; Hulme, C. Tetra-
hedron Lett. 2002, 43, 1637.
(13) (a) Aoki, K.; Obata, T.; Yamazaki, Y.; Mori, Y.; Hirokawa, H.;
Koseki, J.; Hattori, T.; Niitsu, K.; Takeda, S.; Aburada, M.;
Miyamoto, K. Chem. Pharm. Bull. 2007, 55, 255. (b) Aoki, K.;
Koseki, J.; Takeda, S.; Aburada, M.; Miyamoto, K. Chem. Pharm.
Bull. 2007, 55, 922. (c) Han, Y.-Y.; Wu, Z.-J.; Zhang, X.-M.; Yuan,
W.-C. Tetrahedron Lett. 2010, 51, 2023.
Supporting information for this article is available online at
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References
(1) For selected reviews, see: (a) Li, C.-J. Acc. Chem. Res. 2009, 42,
335. (b) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(c) Waterman, R. Chem. Soc. Rev. 2013, 42, 5629. (d) Li, C.-J. From
C–H to C–C Bonds: Cross-Dehydrogenative-Coupling; Royal
Society of Chemistry: Cambridge, 2014. (e) Kozlowski, M. C. Acc.
Chem. Res. 2017, 50, 638. (f) Qin, Y.; Zhu, L.; Luo, S. Chem. Rev.
2017, 117, 9433. (g) Lakshman, M. K.; Vuram, P. K. Chem. Sci.
2017, 8, 5845.
(2) For selected reviews and recent examples, see: (a) Ashenhurst,
J. A. Chem. Soc. Rev. 2010, 39, 540. (b) Le Bras, J.; Muzart, J. Chem.
Rev. 2011, 111, 1170. (c) Shi, Z.; Zhang, C.; Tang, C.; Jiao, N.
Chem. Soc. Rev. 2012, 41, 3381. (d) Song, G.; Wang, F.; Li, X.
Chem. Soc. Rev. 2012, 41, 3651. (e) Mousseau, J. J.; Charette, A. B.
Acc. Chem. Res. 2013, 46, 412. (f) Li, B.; Dixneuf, P. H. Chem. Soc.
Rev. 2013, 42, 5744. (g) Girard, S. A.; Knauber, T.; Li, C. J. Angew.
Chem. Int. Ed. 2014, 53, 74. (h) Yang, Y.; Lan, J.; You, J. Chem. Rev.
2017, 117, 8787. (i) Pan, C.; Huang, B.; Hu, W.; Feng, X.; Yu, J.-T.
J. Org. Chem. 2016, 81, 2087. (j) Sharma, R.; Abdullaha, M.;
Bharate, S. B. J. Org. Chem. 2017, 82, 9786. (k) Chen, X.; Cui, X.;
Yang, F.; Wu, Y. Org. Lett. 2015, 17, 1445. (l) Varun, B. V.;
Dhineshkumar, J.; Bettadapur, K. R.; Siddaraju, Y.; Alagiri, K.;
Prabhu, K. R. Tetrahedron Lett. 2017, 58, 803.
(3) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem.
Rev. 2015, 115, 12138.
(4) For selected examples, see: (a) He, C.-Y.; Fan, S.; Zhang, X. J. Am.
Chem. Soc. 2010, 132, 12850. (b) Gong, X.; Song, G.; Zhang, H.;
Li, X. Org. Lett. 2011, 13, 1766. (c) Wu, Y.; Li, B.; Mao, F.; Li, X.;
Kwong, F. Y. Org. Lett. 2011, 13, 3258. (d) Liu, W.; Li, Y.; Wang,
Y.; Kuang, C. Org. Lett. 2013, 15, 4682. (e) Liu, W.; Yu, X.; Li, Y.;
Kuang, C. Chem. Commun. 2014, 50, 9291. (f) Storr, T. E.;
Namata, F.; Greaney, M. F. Chem. Commun. 2014, 50, 13275.
(g) Bartoccini, F.; Cannas, D. M.; Fini, F.; Piersanti, G. Org. Lett.
2016, 18, 2762. (h) Kianmehr, E.; Fardpour, M.; Kharat, A. N. Eur.
J. Org. Chem. 2017, 3017.
(5) For selected examples, see: (a) Yin, W.; He, C.; Chen, M.; Zhang,
H.; Lei, A. Org. Lett. 2009, 11, 709. (b) Jin, L.-K.; Wan, L.; Feng, J.;
Cai, C. Org. Lett. 2015, 17, 4726. (c) Luo, F.-X.; Cao, Z.-C.; Zhao,
H.-W.; Wang, D.; Zhang, Y.-F.; Xu, X.; Shi, Z.-J. Organometallics
2017, 36, 18. (d) Wang, X.; Xie, P.; Qiu, R.; Zhu, L.; Liu, T.; Li, Y.;
Iwasaki, T.; Au, C.-T.; Xu, X.; Xia, Y.; Yin, S.-F.; Kambe, N. Chem.
Commun. 2017, 53, 8316. (e) Soni, V.; Khake, S. M.; Punji, B. ACS
Catal. 2017, 7, 4202.
(6) For selected examples, see: (a) Li, Z.; Bohle, D. S.; Li, C.-J. Proc.
Natl. Acad. Sci. U.S.A. 2006, 103, 8928. (b) Fan, S.; Chen, Z.;
Zhang, X. Org. Lett. 2012, 14, 4950. (c) Zhang, C.; Tang, C.; Jiao, N.
(14) Utepova, I. A.; Trestsova, M. A.; Chupakhin, O. N.; Charushin, V.
N.; Rempel, A. A. Green Chem. 2015, 17, 4401.
(15) (a) Yotphan, S.; Beukeaw, D.; Reutrakul, V. Synthesis 2013, 45,
936. (b) Buathongjan, C.; Beukeaw, D.; Yotphan, S. Eur. J. Org.
Chem. 2015, 1575. (c) Yotphan, S.; Sumunnee, L.; Beukeaw, D.;
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