Organic Letters
Letter
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(19) For selected examples of metal-mediated or metallic salt-
catalyzed organic reactions developed in our group, see: (a) Shen, Z.
L.; Cheong, H. L.; Loh, T. P. Chem. - Eur. J. 2008, 14, 1875. (b) Wu,
L.-H.; Zhao, K.; Shen, Z.-L.; Loh, T.-P. Org. Chem. Front. 2017, 4,
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(d) Chu, X.-Q.; Cheng, B.-Q.; Zhang, Y.-W.; Ge, D.; Shen, Z.-L.; Loh,
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Doitomi, K.; Ganguly, R.; Li, Y.-X.; Shen, Z.-L.; Hirao, H.; Loh, T.-P.
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(20) Blumke, T. D.; Chen, Y.-H.; Peng, Z.; Knochel, P. Nat. Chem.
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(5) For selected typical examples, see: (a) Rieke, R. D.; Uhm, S. J.
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(21) For a selected review, see: (a) Loh, T.-P.; Chua, G.-L. Chem.
Commun. 2006, 2739. For selected typical examples, see: (b) Peng,
Z.; Blumke, T. D.; Mayer, P.; Knochel, P. Angew. Chem., Int. Ed. 2010,
49, 8516. (c) Shen, Z.-L.; Peng, Z.; Yang, C.-M.; Helberg, J.; Mayer,
P.; Marek, I.; Knochel, P. Org. Lett. 2014, 16, 956. (d) Takai, K.;
Ikawa, Y. Org. Lett. 2002, 4, 1727. (e) Wu, C.; Wang, Z.; Hu, Z.;
Zeng, F.; Zhang, X.-Y.; Cao, Z.; Tang, Z.; He, W.-M.; Xu, X.-H. Org.
Biomol. Chem. 2018, 16, 3177. (f) Chen, B.-Z.; Wang, C.-X.; Jing, Z.-
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(g) Yang, Y.-S.; Shen, Z.-L.; Loh, T.-P. Org. Lett. 2009, 11, 2213.
(22) For selected reviews related to the use of gallium(III) salt in
organic synthesis, see: (a) Prakash, G. K. S.; Mathew, T.; Olah, G. A.
Acc. Chem. Res. 2012, 45, 565. (b) Yamaguchi, M.; Nishimura, Y.
Chem. Commun. 2008, 35. For selected examples, see: (c) Wang, C.-
S.; Fan, T.; Zhang, H.-H.; Li, C.; Shen, Y.; Mei, G.-J.; Shi, F. J. Org.
Chem. 2016, 81, 11734. (d) Cheng, B.-Q.; Zhao, S.-W.; Song, X.-D.;
Chu, X.-Q.; Rao, W.; Loh, T.-P.; Shen, Z.-L. J. Org. Chem. 2019, 84,
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Díaz-Ortiz, A.; Alcazar, J. Green Chem. 2017, 19, 1420. (c) Kloetzing,
R. J.; Thaler, T.; Knochel, P. Org. Lett. 2006, 8, 1125. (d) Greszler, S.
N.; Malinowski, J. T.; Johnson, J. S. J. Am. Chem. Soc. 2010, 132,
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(6) For selected typical examples, see: (a) Fernandez-Ibanez, M. A.;
Macia, B.; Minnaard, A. J.; Feringa, B. L. Angew. Chem., Int. Ed. 2008,
47, 1317. (b) Cozzi, P. G.; Benfatti, F.; Capdevila, M. G.; Mignogna,
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(7) For selected typical examples, see: (a) Chattopadhyay, A.;
Dubey, A. Kr J. Org. Chem. 2007, 72, 9357. (b) Moriwake, T. J. Org.
Chem. 1966, 31, 983.
(8) For selected typical examples, see: (a) Hojo, M.; Harada, H.; Ito,
H.; Hosomi, A. J. Am. Chem. Soc. 1997, 119, 5459. (b) Suh, Y. S.;
Rieke, R. D. Tetrahedron Lett. 2004, 45, 1807. (c) Durandetti, M.;
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(23) For selected typical examples, see: Takai, K.; Kakiuchi, T.;
Utimoto, K. J. Org. Chem. 1994, 59, 2671. Also see ref 21f.
(24) For selected examples for CrCl3-catalyzed reactions, see:
(a) Chen, C.; Liu, P.; Luo, M.; Zeng, X. ACS Catal. 2018, 8, 5864.
(b) Yun, J.-J.; Liu, X.-Y.; Deng, W.; Chu, X.-Q.; Shen, Z.-L.; Loh, T.-
P. J. Org. Chem. 2018, 83, 10898.
Perichon, J. Synthesis 2006, 2006, 1542.
(9) For selected typical examples, see: (a) Orsini, F.; Lucci, E. M.
Tetrahedron Lett. 2005, 46, 1909. (b) Segade, Y.; Montaos, M. A.;
Rodríguez, J.; Jimenez, C. Org. Lett. 2014, 16, 5820. (c) Nelson, C.
G.; Burke, T. R., Jr. J. Org. Chem. 2012, 77, 733.
(10) For a selected typical example, see: Wessjohann, L.; Wild, H.
Synlett 1997, 1997, 731.
(11) For a selected typical example, see: Burkhardt, E.; Rieke, R. D.
J. Org. Chem. 1985, 50, 416.
(12) For a selected typical example, see: Kagoshima, H.; Hashimoto,
Y.; Oguro, D.; Saigo, K. J. Org. Chem. 1998, 63, 691.
(13) For a selected typical example, see: Imamoto, T.; Kusumoto,
T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama,
M. J. Org. Chem. 1984, 49, 3904.
(14) For selected typical examples, see: (a) Chao, L.; Rieke, R. D. J.
Org. Chem. 1975, 40, 2253. (b) Babu, S. A.; Yasuda, M.; Shibata, I.;
Baba, A. Org. Lett. 2004, 6, 4475. (c) Ishihara, J.; Tsuru, H.;
Hatakeyama, S. J. Org. Chem. 2014, 79, 5908. (d) Poisson, T.;
Belhomme, M.-C.; Pannecoucke, X. J. Org. Chem. 2012, 77, 9277.
(15) (a) Knochel, P. Handbook of Functionalized Organometallics;
Wiley-VCH: Weinheim, 2005. (b) Crabtree, R. H.; Mingos, D. M. P.
Comprehensive Organometallic Chemistry III; Elsevier: Oxford, 2007.
(16) For selected reviews of using Fe(II or III) as reaction catalyst,
see: (a) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004,
104, 6217. (b) Correa, A.; García Manchen
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Chem., Int. Ed. 2008, 47, 3317. (d) Sherry, B. D.; Furstner, A. Acc.
Chem. Res. 2008, 41, 1500. (e) Furstner, A. Angew. Chem., Int. Ed.
2009, 48, 1364. (f) Czaplik, W. M.; Mayer, M.; Cvengros, J.; Jacobi
(25) For selected typical examples, see: (a) Piller, F. M.;
Appukkuttan, P.; Gavryushin, A.; Helm, M.; Knochel, P. Angew.
Chem., Int. Ed. 2008, 47, 6802. (b) Krasovskiy, A.; Malakhov, V.;
Gavryushin, A.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 6040.
(c) Shen, Z.-L.; Knochel, P. ACS Catal. 2015, 5, 2324. (d) Bernhardt,
S.; Shen, Z.-L.; Knochel, P. Chem. - Eur. J. 2013, 19, 828. (e) Shen, Z.-
L.; Knochel, P. Chem. - Eur. J. 2015, 21, 7061. (f) Wang, G. J.; Fu, Z.
Q.; Huang, W. Org. Lett. 2017, 19, 3362. (g) Gao, Y. R.; Ma, Y. F.;
Xu, C.; Li, L.; Yang, T. J.; Sima, G. Q.; Fu, Z. Q.; Huang, W. Adv.
Synth. Catal. 2018, 360, 479. (h) Lee, P. H.; Lee, K. Angew. Chem., Int.
Ed. 2005, 44, 3253. (i) Lee, K.; Seomoon, D.; Lee, P. H. Angew.
Chem., Int. Ed. 2002, 41, 3901. (j) Chen, B.-Z.; Zhi, M.-L.; Wang, C.-
X.; Chu, X.-Q.; Shen, Z.-L.; Loh, T.-P. Org. Lett. 2018, 20, 1902.
(k) Liu, X.-Y.; Cheng, B.-Q.; Guo, Y.-C.; Chu, X.-Q.; Li, Y.-X.; Loh,
T.-P.; Shen, Z.-L. Adv. Synth. Catal. 2018, 361, 542.
(26) For selected examples, see: (a) Shen, Z.-L.; Goh, K. K. K.;
Yang, Y.-S.; Lai, Y.-C.; Wong, C. H. A.; Cheong, H.-L.; Loh, T.-P.
Angew. Chem., Int. Ed. 2011, 50, 511. (b) Shen, Z.-L.; Goh, K. K. K.;
Wong, C. H. A.; Yang, Y.-S.; Lai, Y.-C.; Cheong, H.-L.; Loh, T.-P.
Chem. Commun. 2011, 47, 4778. (c) Kim, S.; Kim, C.-E.; Seo, B.; Lee,
P. H. Org. Lett. 2014, 16, 5552. (d) Shen, Z.-L.; Loh, T.-P. Org. Lett.
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(27) For selected examples, see: (a) Pan, X.; Boussonniere, A.;
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Curran, D. P. J. Am. Chem. Soc. 2013, 135, 14433. (b) Yang, F.-L.;
Tian, S.-K. Angew. Chem., Int. Ed. 2013, 52, 4929. (c) Bao, W.-H.; He,
M.; Wang, J.-T.; Peng, X.; Sung, M.; Tang, Z.; Jiang, S.; Cao, Z.; He,
W.-M. J. Org. Chem. 2019, 84, 6065−6071. (d) Wei, T.-Q.; Xu, P.;
von Wangelin, A. ChemSusChem 2009, 2, 396. (g) Bauer, I.; Knolker,
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(17) For selected examples, see: (a) Liu, Y.; Lu, Y.; Prashad, M.;
Repic, O.; Blacklock, T. J. Adv. Synth. Catal. 2005, 347, 217. (b) Gao,
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