Synthesis, Table of Contents Synthesis 2021; 53(06): 1121-1126DOI: 10.1055/s-0040-1706539 paper Ruthenium-Catalyzed Oxidative Dearomatization of N-Boc Indoles Xia Chen a School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, P. R. of China Email: zhouxiaoyu20062006@126.com , Xiao-Yu Zhou∗ a School of Chemistry and Materials Engineering, Liupanshui Normal University, Liupanshui 553004, P. R. of China Email: zhouxiaoyu20062006@126.com , Xiu-Juan Feng b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China , Ming Bao∗ b State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116023, P. R. of China › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Ruthenium-catalyzed oxidative dearomatization of N-Boc indoles for the synthesis of indolin-3-ones is described. The N-Boc indoles can be transformed into indolin-3-ones in acetonitrile, using RuCl3·3H2O as catalyst and sodium periodate (1.5 equiv) as oxidant. Further, a possible mechanism has been proposed on the basis of control experiments. Key words Key words ruthenium - oxidative dearomatization - indoles - indolin-3-ones - sodium periodate Full Text References References 1a Chen I.-S, Chen H.-F, Cheng M.-J, Chang Y.-L, Teng C.-M, Tsutomu I, Chen J.-J, Tsai I.-L. J. Nat. Prod. 2001; 64: 1143 1b Hibino S, Choshi T. Nat. Prod. Rep. 2001; 18: 66 1c Somei M, Yamada F. Nat. Prod. Rep. 2003; 20: 216 1d Kawasaki T, Higuchi K. Nat. Prod. Rep. 2005; 22: 761 1e O’Connor SE, Maresh JJ. Nat. Prod. Rep. 2006; 23: 532 1f Higuchi K, Kawasaki T. Nat. Prod. Rep. 2007; 24: 843 1g Teichert A, Schmidt J, Porzel A, Arnold N, Wessjohann L. J. Nat. Prod. 2008; 71: 1092 1h Höfle G, Böhlendorf B, Fecker T, Sasse F, Kunze B. J. Nat. Prod. 2008; 71: 1967 1i Ishikura M, Yamada K. Nat. Prod. Rep. 2009; 26: 803 1j Li S.-M. Nat. Prod. Rep. 2010; 27: 57 1k Ishikura M, Yamada K, Abe T. Nat. Prod. Rep. 2010; 27: 1630 2a Bur SK, Padwa A. Chem. Rev. 2004; 104: 2401 2b Mąkosza M, Wojciechowski K. Chem. Rev. 2004; 104: 2631 2c Busto E, Gotor-Fernández V, Gotor V. Chem. Rev. 2011; 111: 3998 3a Malapel-Andrieu B, Mérour J.-Y. Tetrahedron 1998; 54: 11095 3b Kawasaki T, Enoki H, Matsumura K, Ohyama M, Inagawa M, Sakamoto M. Org. Lett. 2000; 2: 3027 3c Zhang P, Bierer DE. J. Nat. Prod. 2000; 63: 643 3d Liu Y, McWhorter WW. J. Am. Chem. Soc. 2003; 125: 4240 3e Liu Y, McWhorter WW. J. Org. Chem. 2003; 68: 2618 3f Grougnet R, Magiatis P, Fokialakis N, Mitaku S, Skaltsounis A.-L, Tillequin F, Sévenet T, Litaudon M. J. Nat. Prod. 2005; 68: 1083 3g Wyrembak PN, Hamilton AD. J. Am. Chem. Soc. 2009; 131: 4566 3h Matsumoto M, Samata D, Akazome M, Ogura K. Tetrahedron Lett. 2009; 50: 111 4a Zhang X, Foote CS. J. Am. Chem. Soc. 1993; 115: 8867 4b Colandrea V, Rajaraman JS, Jimenez LS. Org. Lett. 2003; 5: 785 5 Desarbre E, Savelon L, Cornec O, Mérour JY. Tetrahedron 1996; 52: 2983 6a Feigelson GB, Danishefsky SJ. J. Org. Chem. 1988; 53: 3392 6b Gharpure SJ, Sathiyanarayanan AM. Chem. Commun. 2011; 47: 3625 7 Kiraz CI. A, Emge TJ, Jimenaz LS. J. Org. Chem. 2004; 69: 2200 8 Zhang J.-L, Che C.-M. Chem. Eur. J. 2005; 11: 3899 9 Lerch S, Unkel L.-N, Brasholz M. Angew. Chem. Int. Ed. 2014; 53: 6558 10a Guchhait SK, Chaudhary V, Rana VA, Priyadarshani G, Kandekar S, Kashyap M. Org. Lett. 2016; 18: 1534 10b Zhou X.-Y, Chen X, Wang L.-G. Synlett 2016; 27: 2742 10c Zhou X.-Y, Chen X, Wang L.-G, Yang D, Li Z. Synthesis 2017; 49: 3662 11 Jiang X, Yang J, Zhang F, Yu P, Yi P, Sun Y, Wang Y. Org. Lett. 2016; 18: 3154 12 Kong L, Wang M, Zhang F, Xu M, Li Y. Org. Lett. 2016; 18: 6124 13 Zhang C, Li S, Bureš F, Lee R, Ye X, Jiang Z. ACS Catal. 2016; 6: 6853 14 Dhineshkumar J, Gadde K, Prabhu KR. J. Org. Chem. 2018; 83: 228 15 Zhou X.-Y, Chen X, Wang L.-G, Yang D, Li J.-H. Synlett 2018; 29: 835 16 Zhang J, Kohlbouni ST, Borhan B. Org. Lett. 2019; 21: 14 17 Pape AR, Kaliappan KP, Kündig EP. Chem. Rev. 2000; 100: 2917 18 Murahashi SI, Oda Y, Komiya N, Naota T. Tetrahedron Lett. 1994; 35: 7953 Supplementary Material Supplementary Material Supporting Information
