Iron-Catalyzed Direct C(sp³)–H Amination Reactions of Isochroman Derivatives with Primary Arylamines under Mild Conditions

Abstract

A direct C(sp³)–H amination reaction of isochroman derivatives with arylamines was developed in the presence of iron(II) salt. A variety of isochroman derivatives and primary amines were selectively transformed into the corresponding oxidative coupling products in good to excellent yield under mild conditions

Key words

C(sp³)–H amination - isochroman - arylamines - iron

• Reference and Notes


For selected examples, see:
• 1a Armstrong A, Collins JC. Angew. Chem. Int. Ed. 2010; 49: 2282
• 1b Iglesias Á, Pérez EG, Muñiz K. Angew. Chem. Int. Ed. 2010; 49: 8109
• 1c Pan S, Liu J, Li H, Wang Z, Guo X, Li Z. Org. Lett. 2010; 12: 1932
• 1d Sibbald PA, Rosewall CF, Swartz RD, Michael FE. J. Am. Chem. Soc. 2009; 131: 15945
• 1e Su Y, Zhao M, Han K, Song G, Li X. Org. Lett. 2010; 12: 5462
• 1f Xu H, Zhang Y, Huang J, Chen W. Org. Lett. 2010; 12: 3704

For selected examples, see:
• 2a Geraghty NW, Hannan JJ. Tetrahedron Lett. 2001; 42: 3211
• 2b Zhang B, Zhu S.-F, Zhou Q.-L. Tetrahedron 2012; 69: 2033
• 2c Zhang Y, Li CJ. Eur. J. Org. Chem. 2007; 4654

For selected examples, see:
• 3a Aihara Y, Chatani N. J. Am. Chem. Soc. 2013; 135: 5308
• 3b Lee JM, Chang S. Tetrahedron Lett. 2006; 47: 1375
• 3c Lou S.-J, Xu D.-Q, Shen D.-F, Wang Y.-F, Liu Y.-K, Xu Z.-Y. Chem. Commun. 2012; 48: 11993
• 3d Nakao Y, Morita E, Idei H, Hiyama T. J. Am. Chem. Soc. 2011; 133: 3264
• 3e Vuppalapati SV, Lee YR. Tetrahedron 2012; 68: 8286
• 3f Wasa M, Yu J.-Q. Tetrahedron 2010; 66: 4811
• 4a Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 3672
• 4b Li Z, Li H, Guo X, Cao L, Yu R, Li H, Pan S. Org. Lett. 2008; 10: 803
• 4c McQuaid KM, Sames D. J. Am. Chem. Soc. 2008; 131: 402
• 4d Richter H, García Mancheño O. Eur. J. Org. Chem. 2010; 4460
• 4e Zhou G, Liu F, Zhang J. Chem. Eur. J. 2011; 17: 3101
• 5a Cheng D, Bao W. Adv. Synth. Catal. 2008; 350: 1263
• 5b Li Z, Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810
• 5c Niu M, Yin Z, Fu H, Jiang Y, Zhao Y. J. Org. Chem. 2008; 73: 3961
• 6a Li Z, Cao L, Li CJ. Angew. Chem. Int. Ed. 2007; 46: 6505
• 6b Pelletier G, Powell DA. Org. Lett. 2006; 8: 6031
• 6c Zhang Y, Li C.-J. J. Am. Chem. Soc. 2006; 128: 4242
• 7a Baslé O, Li C.-J. Green Chem. 2007; 9: 1047
• 7b Li Z, Li CJ. Eur. J. Org. Chem. 2005; 3173
• 7c Zhang Y, Li CJ. Angew. Chem. 2006; 118: 1983
• 8a Li Z, Li C.-J. J. Am. Chem. Soc. 2005; 127: 6968
• 8b Mo H, Bao W. Adv. Synth. Catal. 2009; 351: 2845
• 8c Pan S, Endo K, Shibata T. Org. Lett. 2011; 13: 4692
• 9a Murahashi S.-I, Komiya N, Terai H, Nakae T. J. Am. Chem. Soc. 2003; 125: 15312
• 9b Volla CM. R, Vogel P. Org. Lett. 2009; 11: 1701
• 9c Xu X, Li X. Org. Lett. 2009; 11: 1027
• 10a Messaoudi S, Brion JD, Alami M. Adv. Synth. Catal. 2010; 352: 1677
• 10b Wei Y, Ding H, Lin S, Liang F. Org. Lett. 2011; 13: 1674
• 10c Xia Q, Chen W. J. Org. Chem. 2012; 77: 9366
• 10d Zhang Y, Fu H, Jiang Y, Zhao Y. Org. Lett. 2007; 9: 3813
• 11 Monguchi D, Fujiwara T, Furukawa H, Mori A. Org. Lett. 2009; 11: 1607
• 12 Wan C, Zhang J, Wang S, Fan J, Wang Z. Org. Lett. 2010; 12: 2338
• 13 Shimizu Y, Obora Y, Ishii Y. Org. Lett. 2010; 12: 1372
• 14 Xia R, Niu H.-Y, Qu G.-R, Guo H.-M. Org. Lett. 2012; 14: 5546
• 15 Gephart RT. III, Huang DL, Aguila MJ, Schmidt G, Shahu A, Warren TH. Angew. Chem. Int. Ed. 2012; 51: 6488
• 16 Wang Z, Mo H, Cheng D, Bao W. Org. Biomol. Chem. 2012; 10: 4249
• 17 Coghlan MJ, Edwards JP, Elmore SW, Jones TK, Kort ME, Kym PR, Moore JL, Pratt JK, Wang AX. US 6506766 (B1), 2003

For selected examples, see:
• 18a Li Z, Yu R, Li H. Angew. Chem. Int. Ed. 2008; 47: 7497
• 18b Guo X, Pan S, Liu J, Li Z. J. Org. Chem. 2009; 74: 8848
• 18c Liu W, Liu J, Ogawa D, Nishihara Y, Guo X, Li Z. Org. Lett. 2011; 13: 6272
• 18d Li Y, Jia F, Li Z. Chem. Eur. J. 2013; 19: 82
• 18e Li Y, Ma L, Jia F, Li Z. J. Org. Chem. 2013; 78: 5638