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Citation: Liu Yang, Lin Liqing, Han Yinghui, Liu Yingjie. Application of Iodine and Iodide in Photocatalysis Organic Synthesis[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4216-4227. doi: 10.6023/cjoc202004053 shu

Application of Iodine and Iodide in Photocatalysis Organic Synthesis

  • a.

    Center of Static Distribution, The Second Affiliated Hospital of Harbin Medical University, Harbin 150081

  • b.

    School of Pharmacy, Harbin University of Commerce, Harbin 150076

  • Corresponding author: Liu Yang, 348596994@qq.com Liu Yingjie, liuyj691@nenu.edu.cn
  • Received Date: 30 April 2020
    Revised Date: 10 June 2020
    Available Online: 24 June 2020

    Fund Project: the Young Innovative Talents of Harbin University of Commerce 2016QN056the Harbin Business University Youth Reserve Talent Project 2019CX36the Excellent Youth Project of Heilongjiang Natural Science Foundation YQ2019B004Project supported by the Excellent Youth Project of Heilongjiang Natural Science Foundation (No. YQ2019B004), the Young Innovative Talents of Harbin University of Commerce (No. 2016QN056) and the Harbin Business University Youth Reserve Talent Project (No. 2019CX36)

Figures(13)

  • Photoredox catalysis has become a universal tool to catalyze a wide variety of chemical reactions with high selectivity under mild conditions. However, traditional photocatalysis relies heavily on photocatalysts with the problems such as high price and environmental pollution. Because iodine and iodide have the advantages of cheap, non-toxic and unique photoreactivity, their application in photochemical synthesis has attracted more and more attention in recent years. The research progress of photo-redox catalysis reactions mediated by iodine and iodide in recent years is summarized, and their future outlook is also discussed.
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    1. [1]

      Hu, A.-Z.; Tang, C.-Q. J. Funct. Mater. 2001, 32, 586(in Chinese).  doi: 10.3321/j.issn:1001-9731.2001.06.008

    2. [2]

      (a) Liu, Y.-Y.; Liang, D.; Lu, L.-Q.; Xiao, W.-J. Chem. Commun. 2019, 55, 4853.
      (b) Li, F.-Y.; Tian, D.; Fan, Y.-F.; Lee, R.; Lu, G.; Yin, Y.; Qiao, B. Nat. Commun. 2019, 10, 1774.
      (c) Cavedon, C.; Madani, A.; Seeberger, P. H.; Perter, B. Org. Lett. 2019, 21, 5331.
      (d) Fabry, D. C.; Zoller, J.; Rueping, M. Org. Chem. Front. 2019, 6, 2635.
      (e) DiMeglio, J. L.; Breuhaus Alvarez, J. L.; Li, S. Q.; Bartlett, B. M. ACS Catal. 2019, 9, 5732.

    3. [3]

      (a) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176.
      (b) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
      (c) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911.

    4. [4]

      (a) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102.
      (b) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828.
      (c) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985.
      (d) Marzo, L.; Pagire, S. K.; Reiser, O. B. Angew. Chem., Int. Ed. 2018, 57, 10034.

    5. [5]

      (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
      (b) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
      (c) Cherevatskaya, M.; König, B. Russ. Chem. Rev. 2014, 83, 183.
      (d) Lang, X.; Chen, X.; Zhao, J. Chem. Soc. Rev. 2014, 43, 473.
      (e) Chen, J.; Cen, J.; Xu, X.; Li, X. Catal. Sci. Technol. 2016, 6, 349.
      (f) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
      (g) Hari, D. P.; Kçnig, B. Chem. Commun. 2014, 50, 6688.
      (h) Fukuzumi, S.; Kotani, H.; Ohkubo, K.; Ogo, S.; Tkachenko, N. V.; Lemmetyinen, H. J. Am. Chem. Soc. 2004, 126, 1600.
      (i) Ghosh, I.; Ghosh, T.; Bardagi, J. I.; König, B. Science 2014, 346, 725.

    6. [6]

      (a) Liu, Y.; Zhang, M.; Tung, C.-H.; Wang, Y. ACS Catal. 2016, 6, 8389.
      (b) Lang, X.; Ma, W.; Chen, C.; Ji, H.; Zhao, J. Acc. Chem. Res. 2014, 47, 355.
      (c) Kisch, H. Angew. Chem., Int. Ed. 2013, 52, 812.
      (d) Fox, M. A.; Dulay, M. T. Chem. Rev. 1993, 93, 341.

    7. [7]

      Lu, Z.; Yoon, T. P. Angew. Chem., Int. Ed. 2012, 51, 10329.  doi: 10.1002/anie.201204835

    8. [8]

    9. [9]

      Brown, R. L.; Klemperer, W. J. Chem. Phys. 1964, 41, 3072.  doi: 10.1063/1.1725680

    10. [10]

      (a) Meadows, L. F.; Noyes, R. M.; J. Am. Chem. Soc. 1960, 82, 1872.
      (b) Olmsted, J.; Karal, G. J. Am. Chem. Soc. 1972, 94, 3305.
      (c) Luther, G. W.; Wu, J.; Cullen, J. B. ACS Catal. 1995, 244, 135.

    11. [11]

      (a) Gopal, P. R.; Prabakar, A. C.; Chandrashekar, E. R. R.; Bhaskar, B. V.; Somaiah, P. V. J. Chin. Chem. Soc. 2013, 60, 639.
      (b) Ghosh, N.; Sheldrake, H. M.; Searcey, M. P. K. Curr. Top. Med. Chem. 2009, 9, 1494.
      (c) Zechmeister, K.; Brandl, F.; Hoppe, W.; Hecker, E.; Opferkuch, H. J.; Adolf, W. Tetrahedron Lett. 1970, 11, 4075.

    12. [12]

      (a) Nani, R. R.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7304.
      (b) Faust, R. Angew. Chem., Int. Ed. 2000, 39, 2495.

    13. [13]

      (a) Gopinath, P.; Chandrasekaran, S. J. Org. Chem. 2011, 76, 700.
      (b) Korotkov, V. S.; Larionov, O. V.; Hofmeister, A.; Magull, J.; de Meijere, A. J. Org. Chem. 2007, 72, 7504.
      (c) Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014.

    14. [14]

      (a) Zhang, Y.; Qian, R.; Zheng, X.; Zeng, Y.; Sun, J.; Chen, Y.; Ding, A.; Guo, H. Chem. Commun. 2015, 51, 54.
      (b) Dao, H. T.; Baran, P. S. Angew. Chem., Int. Ed. 2014, 53, 14382.
      (c) Piou, T.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 11292.
      (d) Alexakis, A.; Krause, N.; Woodward, S. Copper-Catal. Asymmetric Synth. 2014, 20, 3.
      (e) Bartoli, G.; Bencivenni, G.; Dalpozzo, R. Synthesis 2014, 46, 979.

    15. [15]

      (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911.
      (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
      (c) Doyle, M. P. Chem. Rev. 1986, 86, 919.
      (d) Bolsønes, H.; Bonge-Hansen, H.; Bonge-Hansen, T. Synlett 2014, 25, 221.
      (e) Nani, R. R.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 7304.
      (f) Marcoux, D.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2009, 131, 6970.
      (g) Pons, A.; Beucher, H.; Ivashkin, P.; Lemonnier, G.; Poisson, T.; Charette, A. B.; Jubault, P.; Pannecoucke, X. Org. Lett. 2015, 17, 1790.

    16. [16]

      (a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5323.
      (b) Taillemaud, S.; Diercxsens, N.; Gagnon, A.; Charette, A. B. Angew. Chem., Int. Ed. 2015, 54, 14108.

    17. [17]

      Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.  doi: 10.1021/ja01084a034

    18. [18]

      Kulinkovich, O. G.; Sviridov, S. V.; Vasilevski, D. A. Synthesis 1991, 234.

    19. [19]

      (a) Dhakal, R. C.; Dieter, R. K. J. Org. Chem. 2013, 78, 12426.
      (b) Ferrary, T.; David, E.; Milanole, G.; Besset, T.; Jubault, P.; Pannecoucke, X. Org. Lett. 2013, 15, 5598.
      (c) Aitken, L. S.; Hammond, L. E.; Sundaram, R.; Shankland, K.; Brown, G. D.; Cobb, A. J. A. Chem. Commun. 2015, 51, 13558.
      (d) Jiang, K.; Chen, Y. Tetrahedron Lett. 2014, 55, 2049.

    20. [20]

      Usami, K.; Nagasawa, Y.; Yamaguchi, E.; Tada, N.; Itoh, A. Org. Lett. 2016, 18, 8.  doi: 10.1021/acs.orglett.5b02957

    21. [21]

      (a) Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. 1985, 24, 94.
      (b) Picman, A. K. Biochem. Syst. Ecol. 1986, 14, 255.
      (c) Nefkens, G. H. L.; Thuring, J. W. J. F.; Beenakkers, M. F. M.; Zwanenburg, B. J. Agric. Food Chem. 1997, 45, 2273.
      (d) Mangnus, E. M.; Zwanenburg, B. J. J. Agric. Food Chem. 1992, 40, 1066.
      (e) Fang, B.; Xie, X.; Zhao, C.; Jing, P.; Li, H.; Wang, Z.; Gu, J.; She, X. J. Org. Chem. 2013, 78, 6338.

    22. [22]

      Selected examples for Bronsted acid mediated cyclization:(a) Nair, V.; Prabhakaran, J.; George, T. G. Tetrahedron 1997, 53, 15061.
      (b) Taylor, S. K. Synthesis 1998, 1009.
      (c) Ramachandran, P. V.; Krzeminski, M. P.; Reddy, M. V. R.; Brown, H. C. Tetrahedron:Asymmetry 1999, 10, 11.
      (d) Sibrian-Vazquez, M.; Spivak, D. A. Synlett 2002, 1105.
      (e) Zhao, J.; Burgess, K. Org. Lett. 2009, 11, 2053.
      (f) Jha, V.; Kondekar, N. B. Org. Lett. 2010, 12, 2762.
      (g) Qabaja, G.; Wilent, J. E.; Benavides, A. R.; Bullard, G. E.; Peterson, K. S. Org. Lett. 2013, 15, 1266.
      (h) Wilent, J.; Peterson, K. S. J. Org. Chem. 2014, 79, 2303.
      (i) Jha, V.; Kumar, P. RSC Adv. 2014, 4, 3238.

    23. [23]

      Selected examples for Lewis acid mediated cyclization:(a) Yang, C.-G.; Reich, N. W.; Shi, Z.; He, C. Org. Lett. 2005, 7, 4553.
      (b) Yeh, M.-C. P.; Lee, Y.-C.; Young, T.-C. Synthesis 2006, 3621.
      (c) Toullec, P. Y.; Genin, E.; Antoniotti, S.; Genet, J.-P.; Michelet, V. Synlett 2008, 707.
      (d) Gooßen, L. J.; Ohlmann, D. M.; Dierker, M. Green Chem. 2010, 12, 197.
      (e) Valerio, V.; Petkova, D.; Madelaine, C.; Maulide, N. Chem.-Eur. J. 2013, 19, 2606.
      (f) Grover, H. K.; Emmett, M. R.; Kerr, M. A. Org. Lett. 2013, 15, 4838.
      (g) Shu, X.-Z.; Nguyen, S. C.; He, Y.; Oba, F.; Zhang, Q.; Canlas, C.; Somorjai, G. A.; Alivisatos, A. P.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 7083.
      (h) Zheng, M.; Chen, P.; Huang, L.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 5756.

    24. [24]

      Selected examples for oxidative or reductive cyclization:(a) Taylor, S. K.; Chmiel, N. H.; Simons, L. J.; Vyvyan, J. R. J. Org. Chem. 1996, 61, 9084.
      (b) Trend, R. M.; Ramtohul, Y. K.; Ferreira, E. M.; Stolts, B. M. Angew. Chem., Int. Ed. 2003, 42, 2892.
      (c) Tellitu, I.; Serna, S.; Herrero, M. T.; Moreno, I.; Domínguez, E.; SanMartin, R. J. Org. Chem. 2007, 72, 1526.
      (d) Dohi, T.; Takenaga, N.; Goto, A.; Maruyama, A.; Kita, Y. Org. Lett. 2007, 9, 3129.
      (e) Shu, C.; Liu, M.-Q.; Sun, Y.-Z.; Ye, L.-W. Org. Lett. 2012, 14, 4958.
      (f) Tada, N.; Ishigami, T.; Cui, L.; Ban, K.; Miura, T.; Itoh, A. Tetrahedron Lett. 2013, 54, 256.
      (g) Xie, X.; Stahl, S. S. J. Am. Chem. Soc. 2015, 137, 3767.
      (h) Duhamel, T.; Muñiz, K. Chem. Commun. 2019, 55, 933.

    25. [25]

      Selected examples for cyclizative lactonization:(a) Kishida, A.; Nagaoka, H. Tetrahedron Lett. 2008, 49, 6393.
      (b) Murphy, S. K.; Dong, V. M. J. Am. Chem. Soc. 2013, 135, 5553.
      (c) Zhang, Q.-B.; Ban, Y.-L.; Zhou, D.-G.; Zhou, P.-P.; Wu, L.-Z.; Liu, Q. Org. Lett. 2016, 18, 5256.
      (d) Sakai, N.; Horikawa, S.; Ogiwara, Y. RSC Adv. 2016, 6, 81763.

    26. [26]

      Maejima, S.; Yamaguchi, E.; Itoh, A. ACS Omega 2019, 4, 4856.  doi: 10.1021/acsomega.9b00333

    27. [27]

      Maejima, S.; Yamaguchi, E.; Itoh, A. J. Org. Chem. 2019, 84, 9519.  doi: 10.1021/acs.joc.9b01081

    28. [28]

      Takedaa, M.; Maejima, S.; Yamaguchi, E.; Itoh, A. Tetrahedron 2019, 60, 151284.  doi: 10.1016/j.tetlet.2019.151284

    29. [29]

      For reviews on the reactions of alkynes, see: (a) Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285.
      (b) Muller, T. E.; Hultzsch, K. C.; Yus, M.; Foubelo, F.; Tada, M. Chem. Rev. 2008, 108, 3795.
      (c) Willis, M. C. Chem. Rev. 2010, 110, 725.
      (d) Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937.
      (e) Gilmore, K.; Alabugin, I. V. Chem. Rev. 2011, 111, 6513.
      (f) Wille, U. Chem. Rev. 2013, 113, 813.
      (g) Salvio, R.; Moliterno, M.; Bella, M. Asian J. Org. Chem. 2014, 3, 340.
      (h) Quintero-Duque, S.; Dyballa, K. M.; Fleischer, I. Tetrahedron Lett. 2015, 56, 2634.
      (i) Gao, P.; Song, X.-R.; Liu, X.-Y.; Liang, Y.-M. Chem.-Eur. J. 2015, 21, 7648.
      (j) Besset, T.; Poisson, T.; Pannecoucke, X. Eur. J. Org. Chem. 2015, 2765.
      (k) Hassan, S.; Mueller, T. J. J. Adv. Synth. Catal. 2015, 357, 617.
      (l) Fang, G.; Bi, X. Chem. Soc. Rev. 2015, 44, 8124.

    30. [30]

      For reviews on C≡C cleavage, see: (a) Yorimitsu, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2009, 82, 778.
      (b) Murakami, M.; Matsuda, T. Chem. Commun. 2011, 47, 1100.
      (c) Assa, C. Synthesis 2011, 3389.
      (d) Ruhland, K. Eur. J. Org. Chem. 2012, 2683.
      (e) Allpress, C. J.; Berreau, L. M. Coord. Chem. Rev. 2013, 257, 3005.
      (f) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613.
      (g) Liu, H.; Feng, M.; Jiang, X. Chem.-Asian. J. 2014, 9, 3360.
      (h) Marek, I.; Masarwa, A.; Delaye, P.-O.; Leibeling, M. Angew. Chem., Int. Ed. 2015, 54, 414.

    31. [31]

      (a) Adams, H.; Guio, L. V. Y.; Morris, M. J.; Spey, S. E. J. Chem. Soc., Dalton Trans. 2002, 2907.
      (b) Chamberlin, R. L. M.; Rosenfeld, D. C.; Wolczanski, P. T.; Lobkovsky, E. B. Organometallics 2002, 21, 2724.
      (c) Hayashi, N.; Ho, D. M.; Pascaljr, R. A. Tetrahedron Lett. 2000, 41, 4261.
      (d) Cairns, G. A.; Carr, N.; Green, M.; Mahon, M. F. Chem. Commun. 1996, 2431
      (e) OÏConnor, J. M.; Pu, L. J. Am. Chem. Soc. 1990, 112, 9013.
      (f) Moriarty, R. M.; Penmasta, R.; Awasthi, X. A. K.; Prakash, I. J. Org. Chem. 1988, 53, 6124.
      (g) Sawaki, Y.; Inoue, H.; Ogata, Y. Bull. Chem. Soc. Jpn. 1983, 56, 1133.
      (h) Sullivan, B. P.; Smythe, R. S.; Kober, E. M.; Meyer, T. J. J. Am. Chem. Soc. 1982, 104, 4701.

    32. [32]

      Dighea, S. U.; Batra, S. Adv. Synth. Catal. 2016, 358, 500.  doi: 10.1002/adsc.201500906

    33. [33]

      For selected examples, see: (a) Sato, A.; Morishita, T.; Shiraki, T.; Yoshioka, S.; Horikoshi, H.; Kuwano, H.; Hanzawa, H.; Hata, T. J. Org. Chem. 1993, 58, 7632.
      (b) Carroll, A. R.; Hyde, E.; Smith, J.; Quinn, R. J.; Guymer, G.; Forster, P. I. J. Org. Chem. 2005, 70, 1096.
      (c) O'Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532.
      (d) Stempel, E.; Gaich, T. Acc. Chem. Res. 2016, 49, 2390.

    34. [34]

      For selected reviews and book, see: (a) Culkin, D. A.; Hartwig, J. F. Acc. Chem. Res. 2003, 36, 234.
      (b) Johansson, C. C. C.; Colacot, T. J. Angew. Chem., Int. Ed. 2010, 49, 676.

    35. [35]

      (a) Chatgilialoglu, C.; Ferreri, C.; Ballestri, M.; Curran, D. P. Tetrahedron Lett. 1996, 37, 6387.
      (b) Clive, D. L. J.; Paul, C. C.; Wang, Z. J. Org. Chem. 1997, 62, 7028.
      (c) Miura, K.; Fujisawa, N.; Saito, H.; Wang, D.; Hosomi, A. Org. Lett. 2001, 3, 2591.
      (d) Usugi, S.; Yorimitsu, H.; Oshima, K. Tetrahedron Lett. 2001, 42, 4535.
      (e) Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. J. Org. Chem. 2001, 66, 7776.
      (f) Tanaka, S.; Nakamura, T.; Yorimitsu, H.; Oshima, K. Synlett 2002, 569.
      (g) Cai, Y.; Roberts, B. P. Tetrahedron Lett. 2003, 44, 4645.
      (h) Cai, Y.; Roberts, B. P.; Tocher, D. A.; Barnett, S. A. Org. Biomol. Chem. 2004, 2, 2517.
      (i) Takami, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2004, 6, 4555.
      (j) Song, H.-J.; Lim, C. J.; Kim, S. Chem. Commun. 2006, 2893.
      (k) Beckwith, A. L. J.; Schiesser, C. H. Org. Biomol. Chem. 2011, 9, 1736.
      (l) Klos, M. R.; Kazmaier, U. Eur. J. Org. Chem. 2013, 2013, 1726.

    36. [36]

      Sudo, Y.; Yamaguchi, E.; Itoh, A. Org. Lett. 2017, 19, 1610.  doi: 10.1021/acs.orglett.7b00428

    37. [37]

      (a) Cabrele, C.; Reiser, O. J. Org. Chem. 2016, 81, 10109.
      (b) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960.

    38. [38]

      (a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
      (b) Felpin, F. X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693.
      (c) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
      (d) Ritchie, T. J.; Macdonald, S. J. F.; Young, R. J.; Pickett, S. D. Drug Discovery Today 2011, 16, 164.

    39. [39]

      Zhang, H.-W.; Muñiz, K. ACS Catal. 2017, 7, 4122.  doi: 10.1021/acscatal.7b00928

    40. [40]

      (a) Saikia, I.; Borah, A. J.; Phukan, P. Chem. Rev. 2016, 116, 6837.
      (b) Djerassi, C. Chem. Rev. 1948, 43, 271.
      (c) Skell, P. S.; Day, J. C. Acc. Chem. Res. 1978, 11, 381.

    41. [41]

      Cavallo, G.; Metrangolo, P.; Milani, R.; Pilati, T.; Priimagi, A.; Resnati, G.; Terraneo, G. Chem. Rev. 2016, 116, 2478.  doi: 10.1021/acs.chemrev.5b00484

    42. [42]

      Breugst, M.; Detmar, E.; vonder Heiden, D. ACS Catal. 2016, 6, 3203.  doi: 10.1021/acscatal.6b00447

    43. [43]

      Tsuji, N.; Kobayashi, Y.; Takemoto, Y. Chem. Commun. 2014, 50, 13691.  doi: 10.1039/C4CC06014H

    44. [44]

      (a) Svensson, P. H.; Kloo, L. Chem. Rev. 2003, 103, 16494.
      (b) de Violet, P. F. Rev. Chem. Intermed. 1981, 4, 121.

    45. [45]

      (a) Yamada, K.; Kato, T.; Hirata, Y. J. Chem. Soc., Chem. Commun. 1969, 1479.
      (b). Tada, N.; Cui, L.; Ishigami, T.; Ban, K.; Miura, T.; Itoh, A. Green Chem. 2012, 14, 3007.
      (c) Hou, R.-S.; Wang, H.-M.; Lin, Y.-C.; Chen, L.-C. J. Chin. Chem. Soc. 2005, 52, 1029.
      (d) Hou, R.-S.; Wang, H.-M.; Lin, Y.-C.; Chen, L.-C. Heterocycles 2005, 65, 649.
      (e) Uyanik, M.; Yasui, T.; Ishihara, K. Bioorg. Med. Chem. Lett. 2009, 19, 3848.
      (f) Shah, A. A.; Khan, Z. A.; Choudhary, N.; Loholter, C.; Schafer, S.; Marie, G. P. L.; Farooq, U.; Witulski, B.; Wirth, T. Org. Lett. 2009, 11, 3578.
      (g) Farooq, U.; Schafer, S.; Shah, A. A.; Freudendahl, D. M.; Wirth, T. Synthesis 2010, 1023.
      (h) Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
      (i) Uyanik, M.; Ishihara, K. ChemCatChem 2012, 4, 177.

    46. [46]

      Tada, N.; Ishigami, T.; Cui, L.; Ban, K.; Miura, T.; Itoh, A. Tetrahedron Lett. 2013, 54, 256.  doi: 10.1016/j.tetlet.2012.11.014

    47. [47]

      Selvam, T. P.; Kumar, P. V. Res. Pharm. 2011, 1, 1.

    48. [48]

      (a) Gundla, R.; Kazemi, R.; Sanam, R.; Muttineni, R.; Sarma, J. A. R. P.; Dayam, R.; Neamati, N. J. Med. Chem. 2008, 51, 3367.
      (b) Mendes da Silva, J. F.; Walters, M.; Al-Damluji, S.; Ganellin, C. R. Bioorg. Med. Chem. 2008, 16, 7254.

    49. [49]

      (a) Wendlandt A. E.; Stahl, S. S. J. Am. Chem. Soc. 2014, 136, 506.
      (b) Chen, Z.; Chen, J.; Liu, M.; Ding, J.; Gao, W.; Huang, X.; Wu, H. J. Org. Chem. 2013, 78, 11342.
      (c) Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U. W.; Orru, R. V. A.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058.
      (d) Rachakonda, S.; Pratap, P. S.; Rao, M. V. B. Synthesis 2012, 44, 2065.
      (e) Yan, Y.; Wang, Z. Chem. Commun. 2011, 47, 9513.
      (f) Han, B.; Wang, C.; Han, R.-F.; Yu, W.; Duan, X.-Y.; Fang, R.; Yang, X.-L. Chem. Commun. 2011, 47, 7818.
      (g) Karnakar, K.; Shankar, J.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D. Synlett 2011, 1089.
      (h) Zhang, J.; Yu, C.; Wang, S.; Wan, C.; Wang, Z. Chem. Coommun. 2010, 46, 5244.
      (i) Zhang, J.; Yu, C.; Wang, S.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841.
      (j) Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. J. Org. Chem. 2009, 74, 4934.
      (k) Portela-Cubillo, F.; Scott, J. S.; Walton, J. C. Chem. Commun. 2008, 2935.
      (l) Ferrini, S.; Ponticelli, F.; Taddei, M. Org. Lett. 2007, 9, 69.

    50. [50]

      Han, B.; Yang, X.-L.; Wang, C.; Bai, Y.-W.; Pan, T.-C.; Chen, X.; Yu, W. J. Org. Chem. 2012, 77, 1136.  doi: 10.1021/jo2020399

    51. [51]

      Fang, J.; Zhou, J.; Fang, Z. RSC Adv. 2013, 3, 334.  doi: 10.1039/C2RA22278G

    52. [52]

      Maheswari, C. U.; Kumar, G. S.; Venkateshwar, M.; Kumar, R. A.; Kantam, M. L.; Reddy, K. R. Adv. Synth. Catal. 2010, 352, 341.  doi: 10.1002/adsc.200900715

    53. [53]

      Vanden Eynde, J. J.; Godin, J.; Mayence, A.; Maquestiau, A.; Anders, E. Synthesis 1993, 867.

    54. [54]

      Peng, Y.; Zeng, Y.; Qiu, G.; Cai, L.; Pike, V. W. J. Heterocycl. Chem. 2010, 47, 1240.  doi: 10.1002/jhet.444

    55. [55]

      Yamaguchi, T.; Sakairi, K.; Yamaguchi, E.; Tada, N.; Itoh, A. RSC Adv. 2016, 6, 56892.  doi: 10.1039/C6RA04073J

    56. [56]

      Vitaku, E.; Smith, D. T.; Njardarson, J. T. J. Med. Chem. 2014, 57, 10257.  doi: 10.1021/jm501100b

    57. [57]

      (a) Minisci, F.; Galli, R.; Cecere, M.; Malatesta, V.; Caronna, T. Tetrahedron Lett. 1968, 9, 5609.
      (b) Minisci, F.; Vismara, E.; Fontana, F. Heterocycles 1989, 28, 489.
      (c) Minisci, F.; Fontana, F.; Vismara, E. J. Heterocycl. Chem. 1990, 27, 79.

    58. [58]

    59. [59]

      Fu, M.-C.; Shang, R.; Zhao, B.; Wang, B.; Fu, Y. Science 2019, 363, 1429.  doi: 10.1126/science.aav3200

    60. [60]

      Fu, Y.; Liu, L.; Yu, H.-Z.; Wang, Y.-M.; Guo, Q.-X. J. Am. Chem. Soc. 2005, 127, 7227.  doi: 10.1021/ja0421856

    61. [61]

      Noble, A.; Aggarwal, V. K. Sci. China:Chem. 2019, 62, 1083.  doi: 10.1007/s11426-019-9489-4

    62. [62]

      (a) Stang, P. J.; Zhdankin, V. V. Chem. Rev. 1996, 96, 1123.
      (b) Zhdankin, V. V. Curr. Org. Synth. 2005, 2, 121.
      (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
      (d) Wu, S. W.; Liu, J. L.; Liu, F. Org. Lett. 2016, 18, 1.

    63. [63]

      For selected reviews and papers: (a) Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003.
      (b) Singh, G. S.; Desta, Z. Y. Chem. Rev. 2012, 132, 6104.
      (c) Dalpozzo, R.; Bartoli, G.; Bencivenni, G. Chem. Soc. Rev. 2012, 41, 7247.
      (d) Song, R.-J.; Liu, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2015, 47, 1195.

    64. [64]

      For selected examples: (a) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748.
      (b) Jia, Y.-X.; Kündig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636.
      (c) Piou, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2012, 51, 11561.

    65. [65]

      For selected reviews: (a) Kolb, H. C.; Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
      (b) Beccalli, E. M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107, 5318.
      (c) Muňiz, K. Angew. Chem., Int. Ed. 2009, 48, 9412.
      (d) McDonald, R. I.; Liu, G.; Stahl, S. S. Chem. Rev. 2011, 111, 2981.
      (e) Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464.
      (f) Chen, J.-R.; Yu, X.-Y.; Xiao, W.-J. Synthesis 2015, 47, 604.

    66. [66]

      Ji, W.-Q.; Tan, H.; Wang, M.; Li, P.-H.; Wang, L. Chem. Commun. 2016, 52, 1462.  doi: 10.1039/C5CC08253F

    67. [67]

      Seoud, O. A.; Ferreira, M.; Rodrigues, W. A.; Ruasse, M. F. J. Phys. Org. Chem. 2005, 18, 173.  doi: 10.1002/poc.864

    68. [68]

      (a) Ochiai, M.; Ito, T.; Takahashi, H.; Nakanishi, A.; Toyonari, M.; Sueda, T.; Goto, S.; Shiro, M. J. Am. Chem. Soc. 1996, 118, 7716.
      (b) Do, H.-Q.; Kashif Khan, R. M.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185.
      (c) Moteki, S. A.; Usui, A.; Selvakumar, S.; Zhang, T.; Maruoka, K. Angew. Chem., Int. Ed. 2014, 53, 11060.

    69. [69]

      (a) Li, H.; Li, P.; Tan, H.; Wang, L. Chem.-Eur. J. 2013, 19, 14432.
      (b) Chen, L.; Li, H.; Yu, F.; Wang, L. Chem. Commun. 2014, 50, 14866.

    70. [70]

      (a) Xie, J.; Xu, P.; Li, H.; Xue, Q.; Jin, H.; Cheng, Y.; Zhu, C. Chem. Commun. 2013, 49, 5672.
      (b) Tan, H.; Li, H.; Ji, W.; Wang, L. Angew. Chem., Int. Ed. 2015, 54, 8374.

    71. [71]

      (a) Murakami, A.; Gao, G.; Omura, M.; Yano, M.; Ito, C.; Furukawa, H.; Takahashi, D.; Koshimizu, K.; Ohigashi, H. Bioorg. Med. Chem. Lett. 2000, 10, 59.
      (b) Wang, C. J.; Hsieh, Y. J.; Chu, C. Y.; Lin, Y. Y.; Tseng, T. H. Cancer Lett. 2002, 183, 163.
      (c) Zhao, Y.; Zheng, Q.; Dakin, K.; Xu, K.; Martinez, M. L.; Li, W. H. J. Am. Chem. Soc. 2004, 126, 4653.
      (d) Borges, F.; Roleira, F.; Milhazes, N.; Santana, L.; Uriarte, E. Curr. Med. Chem. 2005, 12, 887.
      (e) Signore, G.; Nifosi, R.; Albertazzi, L.; Storti, B.; Bizzarri, R. J. Am. Chem. Soc. 2010, 132, 1276.
      (f) Wang, C.; Wu, C.; Zhu, J.; Miller, R. H.; Wang, Y. J. Med. Chem. 2011, 54, 2331.
      (g) Sashidhara, K. V.; Kumar, A.; Chatterjee, M.; Rao, K. B.; Singh, S.; Verma, A. K.; Palit, G. Bioorg. Med. Chem. Lett. 2011, 21, 1937.
      (h) Peng, X.; Damu, G.; Zhou, C. Curr. Pharm. Des. 2013, 19, 3884.
      (i) Sandhu, S.; Bansal, Y.; Silakari, O.; Bansal, G. Bioorg. Med. Chem. 2014, 22, 3806.

    72. [72]

      (a) Harayama, T.; Katsuno, K.; Nishiok, H.; Fujii, M.; Nishita, Y.; Ishii, H.; Kaneko, Y. Heterocycles 1994, 39, 613.
      (b) Kadnikov, D. V.; Larock, R. C. Org. Lett. 2000, 2, 3643.
      (c) Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 5139.
      (d) Oyamada, J.; Kitamura, T. Tetrahedron 2006, 62, 6918.
      (e) Surya, P. R. H.; Sivakumar, S. J. Org. Chem. 2006, 71, 8715.
      (f) Zhang, L.; Meng, T.; Fan, R.; Wu, J. J. Org. Chem. 2007, 72, 7279.
      (g) Yuan, H.-J.; Wang, M.; Liu, Y.-J.; Liu, Q. Adv. Synth. Catal. 2009, 351, 112.
      (h) Yuan, H.; Wang, M.; Liu, Y.; Wang, L.; Liu, J.; Liu, Q. Chem.-Eur. J. 2010, 16, 13450.
      (i) Raju, B.-C.; Tiwari, A.-K.; Kumar, J.-K.; Ali, A.-Z.; Agawane, S.-B.; Saidachary, G.; Madhusudana, K. Bioorg. Med. Chem. 2010, 18, 358.
      (j) Fernandes, T. A.; GontijoVaz, B.; Eberlin, M. N.; Silva, A. J. M.; Costa, P. R. R. J. Org. Chem. 2010, 75, 7085.
      (k) Yan, K.; Yang, D.; Wei, W.; Wang, F.; Shuai, Y.; Li, Q.; Wang, H. J. Org. Chem. 2015, 80, 1550.

    73. [73]

      Yang, S.; Tan, H.; Ji, W.-Q.; Zhang, X.-B.; Li, P.-H.; Wang, L. Adv. Synth. Catal. 2017, 359, 1.  doi: 10.1002/adsc.201601440

    74. [74]

      Huang, H.; Zhang, G.; Chen, Y. Angew. Chem., Int. Ed. 2015, 54, 7872.  doi: 10.1002/anie.201502369

    75. [75]

      (a) Matcha, K.; Narayan, R.; Antonchick, A. P. Angew. Chem., Int. Ed. 2013, 52, 7985.
      (b) Do, H.-Q.; Kashif Khan, R. M.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185.
      (c) Moteki, S. A.; Usui, A.; Selvakumar, S.; Zhang, T.; Maruoka, K. Angew. Chem., Int. Ed. 2014, 53, 11060.

    76. [76]

      (a) Meanwell, N. A. J. Med. Chem. 2011, 54, 2529.
      (b) Carlo, B.; Donna, M. H.; Amos, B. S. Chem. Med. Chem. 2013, 8, 385.
      (c) Ballatore, C.; Soper, J. H.; Piscitelli, F.; James, M.; Huang, L.; Atasoylu, O.; Huryn, D. M.; Trojanowski, J. Q.; Lee, V. M.; Brunden, K. R.; Smith, A. B. J. Med. Chem. 2011, 54, 6969.
      (d) Malwal, S. R.; Sriram, D.; Yogeeswari, P.; Konkimalla, V. B.; Chakrapani, H. J. Med. Chem. 2012, 55, 553.
      (e) Feng, M.; Tang, B.; Liang, S. H.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
      (f) Adhikari, N.; Mukherjee, A.; Saha, A.; Jha, T. Eur. J. Med. Chem. 2017, 129, 72.

    77. [77]

      (a) Wynne, J. H.; Price, S. E.; Rorer, J. R.; Stalick, W. M. Synth. Commun. 2003, 33, 341.
      (b) Khalafi-Nezhad, A.; Parhami, A.; Zare, A.; Shirazi, A. N.; Zare, A. R. M.; Hassaninejad, A. Can. J. Chem. 2008, 86, 456.
      (c) Wu, X.-F.; Vovard-Le Bray, C.; Bechki, L.; Darcel, C. Tetrahedron 2009, 65, 7380.
      (d) Chang, J. W. W.; Ton, T. M. U.; Tania, S.; Taylor, P. C.; Chan, P. W. H. Chem. Commun. 2010, 46, 922.
      (e) Chawla, R.; Singh, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2014, 55, 3553.
      (f) Morales, S.; Guijarro, F. G.; Garcia Ruano, J. L.; Cid, M. B. J. Am. Chem. Soc. 2014, 136, 1082.
      (g) Reeves, J. T.; Visco, M. D.; Marsini, M. A.; Grinberg, N.; Busacca, C.A.; Mattson, A. E.; Senanayake, C. H. Org. Lett. 2015, 17, 2442.
      (h) Sharghi, H.; Hosseini-Sarvari, M.; Ebrahimpourmoghaddam, S. ARKIVOC 2007, xv, 255.

    78. [78]

      (a) Sisko, J.; Weinreb, S. M. J. Org. Chem. 1990, 55, 393.
      (b) Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468.
      (c) Huang, D.; Wang, X.; Wang, X.; Chen, W.; Wang, X.; Hu, Y. Org. Lett. 2016, 18, 604.

    79. [79]

      (a) Hopkins, M. D.; Scott, K. A.; DeMier, B. C.; Morgan, H. R.; Macgruder, J. A.; Lamar, A. A. Org. Biomol. Chem. 2017, 15, 9209.
      (b) Zard, S. Z. Chem. Soc. Rev. 2008, 37, 1603.
      (c) Höfling, S. B.; Heinrich, M. R. Synthesis 2011, 173.
      (d) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Soc. Rev. 2016, 45, 2044.
      (e) Achar, T. K.; Mal, P. J. Org. Chem. 2015, 80, 666.
      (f) Jin, L. M.; Lu, H.; Cui, Y.; Lizardi, C. L.; Arzua, T. N.; Wojtas, L.; Cui, X.; Zhang, X. P. Chem. Sci. 2014, 5, 2422.
      (g) Liu, Z.; Zhang, J.; Chen, S.; Shi, E.; Xu, Y.; Wan, X. Angew. Chem. 2012, 51, 3231.

    80. [80]

      Hopkins, M. D.; Brandeburg, Z. C.; Hanson A. J.; Lamar, A. A. Molecules 2018, 23, 1838.  doi: 10.3390/molecules23081838

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