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Synlett 2013; 24(15): 1959-1962
DOI: 10.1055/s-0033-1339448
DOI: 10.1055/s-0033-1339448
letter
Copper-Catalyzed Direct N-Arylation of Naphthalimides Using Diaryliodonium Salts
Authors
Further Information
Publication History
Received: 07 May 2013
Accepted after revision: 18 June 2013
Publication Date:
07 August 2013 (online)
Abstract
An effective copper-catalyzed N-arylation of naphthal-imides with diaryliodonium salts in toluene at 100 °C has been developed. This cross-coupling reaction gives the desired N-arylated 1,8-naphthalimides in moderate to good yields. The synthetic potential of this coupling is applied in functional materials based on N-arylated 1,8-naphthalimides, such as molecular probes.
Key words
arylation - copper catalysis - diaryliodonium salts - naphthalimides - C–N cross couplingSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information (PDF)
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References and Notes
- 1a Amino Group Chemistry, From Synthesis to the Life Sciences. Ricci A. Wiley-VCH; Weinheim: 2008
- 1b Bellmann E, Shaheen SE, Thayumanavan S, Barlow S, Grubbs RH, Marder SR, Kippelen B, Peyghambarian N. Chem. Mater. 1998; 10: 1668
- 3a Muci AR, Buchwald SL. Top. Curr. Chem. 2002; 219: 131
- 3b Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
- 3c Zhang M, Zhang A. Synthesis 2012; 44: 1
- 3d Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
- 3e Sadig JE. R, Willis MC. Synthesis 2011; 1
- 3f Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
- 3g Hartwig JF. Nature 2008; 455: 314
- 4a Morphy R, Rankovic Z. J. Med. Chem. 2005; 48: 6523
- 4b Wexler RR, Greenlee WJ, Irvin JD, Goldberg MR, Prendergast K, Smith RD, Timmermans PB. M. W. M. J. Med. Chem. 1996; 39: 625
- 4c Schnurch M, Flasik R, Khan AF, Spina M, Mihovilovic MD, Stanetty P. Eur. J. Org. Chem. 2006; 15: 3283
- 4d Surry DS, Buchwald SL. Angew. Chem. Int. Ed. 2008; 47: 6338
- 4e Hartwig JF. Acc. Chem. Res. 2008; 41: 1534
- 4f Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
Reference Ris Wihthout Link
- 4g Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651
- 4h Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
- 4i Meldal M, Tornoe CW. Chem. Rev. 2008; 108: 2952
Reference Ris Wihthout Link
- 4j Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
- 4k Wurtz S, Glorius F. Acc. Chem. Res. 2008; 41: 1523
- 4l Ley SV, Thomas AW. Angew. Chem. Int. Ed. 2003; 42: 5400
Reference Ris Wihthout Link
- 5a Zhdankin VV, Stang PJ. Chem. Rev. 2002; 102: 2523
- 5b Zhdankin VV, Stang PJ. Chem. Rev. 2008; 108: 5299
- 5c Merritt EA, Olofsson B. Angew. Chem. Int. Ed. 2009; 48: 9052 ; Angew. Chem. 2009, 121, 9214
Reference Ris Wihthout Link
- 5d Silva LF, Olofsson B. Nat. Prod. Rep. 2011; 28: 1722
- 5e Yusubov MS, Zhdankin VV. Curr. Org. Synth. 2012; 9: 247
- 6a Kang SK, Lee SH, Lee D. Synlett 2000; 1022
- 6b Beletskaya IP, Davydov DV, Gorovoy MS. Tetrahedron Lett. 2002; 43: 6221
- 6c Zhou T, Chen ZC. Synth. Commun. 2002; 32: 903
- 6d Wang FY, Chen ZC, Zheng QG. J. Chem. Res. 2004; 206
- 6e Niu HY, Xia C, Qu GR, Zhang Q, Jiang Y, Mao RZ, Li DY, Guo HM. Org. Biomol. Chem. 2011; 9: 5039
- 6f Vaddula B, Leazer J, Varma RS. Adv. Synth. Catal. 2012; 354: 986
- 7a Beringer FM, Galton SA. J. Org. Chem. 1963; 28: 3417
- 7b Hampton KG, Harris TM, Hauser CR. J. Org. Chem. 1964; 29: 3511
- 7c Chen K, Koser GF. J. Org. Chem. 1991; 56: 5764
- 7d Gao P, Portoghese PS. J. Org. Chem. 1995; 60: 2276
- 7e Ryan JH, Stang PJ. Tetrahedron Lett. 1997; 38: 5061
- 7f Iwama T, Birman VB, Kozmin SA, Rawal VH. Org. Lett. 1999; 1: 673
- 7g Oh CH, Kim JS, Jung HH. J. Org. Chem. 1999; 64: 1338
- 7h Allen AE, MacMillan DW. C. J. Am. Chem. Soc. 2011; 133: 4260
- 7i Harvey JS, Simonovich SP, Jamison CR, MacMillan DW. C. J. Am. Chem. Soc. 2011; 133: 13782
- 7j Bigot A, Williamson AE, Gaunt MJ. J. Am. Chem. Soc. 2011; 133: 13778
- 7k Skucas E, MacMillan DW. C. J. Am. Chem. Soc. 2012; 134: 9090
- 8a Kalyani D, Deprez NR, Desai LV, Sanford MS. J. Am. Chem. Soc. 2005; 127: 7330
- 8b Deprez NR, Kalyani D, Krause A, Sanford MS. J. Am. Chem. Soc. 2006; 128: 4972
- 8c Phipps RJ, Grimster NP, Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 8172
Reference Ris Wihthout Link
- 8d Deprez NR, Sanford MS. J. Am. Chem. Soc. 2009; 131: 11234
- 8e Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
- 8f Xiao B, Fu Y, Xu J, Gong JJ, Dai JY, Liu L. J. Am. Chem. Soc. 2010; 132: 468
- 8g Ciana CL, Phipps RJ, Brandt JR, Meyer FM, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 458 ; Angew. Chem. 2011, 123, 478
- 8h Duong HA, Gilligan RE, Cooke ML, Phipps RJ, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 463 ; Angew. Chem. 2011, 123, 483
- 9a Kitamura T, Yamane M, Inoue K, Todaka M, Fukatsu N, Meng Z, Fujiwara Y. J. Am. Chem. Soc. 1999; 121: 11674
- 9b Xue J, Huang X. Synth. Commun. 2007; 37: 2179
- 10a Grabtchev I, Philipova T. Dyes Pigments 1994; 27: 321
- 10b Bojinov V, Konstantinova T. Dyes Pigments 2002; 54: 239
- 11 Philipova T. J. Prakt. Chem. 1994; 336: 587
- 12 Wolarz E, Moryson H, Bauman D. Displays 1992; 13: 171
- 13 Chang SC, Archer BJ, Utecht RE, Lewis DE, Judy MM, Matthews JL. Bioorg. Med. Chem. Lett. 1993; 3: 555
- 14 Qian X, Tang J, Zhang J. Dyes Pigments 1994; 25: 109
- 15a Walker MA. J. Org. Chem. 1995; 60: 5352
- 15b Walker MA. Tetrahedron Lett. 1994; 35: 665
- 15c Corrie JE. T. J. Chem. Soc., Perkin Trans. 1 1994; 2975
- 15d Mehta NB, Phillips AP, Lui FF, Brooks RE. J. Org. Chem. 1960; 25: 1012
- 15e Aubert T, Farnier M, Guilard R. Tetrahedron 1991; 47: 53
- 16a Upadhyay SK, Pingali SR. K, Jursic BS. Tetrahedron Lett. 2010; 51: 2215
- 16b Machado KE, Oliveria KN, Santos-Bubniak L, Licinio MA, Nunes RJ, Santos-Silva MC. Bioorg. Med. Chem. 2011; 19: 6285
- 16c Zhang Y, Feng SB, Wang K, Yi XH, Wang HS, Pan YM. Synth. Commun. 2012; 42: 3042
- 16d Cao H, Chang V, Hernandez R, Heagy MD. J. Org. Chem. 2005; 70: 4929
- 17 Chernick ET, Ahrens MJ, Scheidt KA, Wasielewski MR. J. Org. Chem. 2005; 70: 1486
- 18 Takács A, Ács P, Kollár L. Tetrahedron 2008; 64: 983
- 19a Kim HJ, Kim J, Cho SH, Chang S. J. Am. Chem. Soc. 2011; 133: 16382
- 19b Kantak AA, Potavathri S, Barham RA, Romano KM, DeBoef B. J. Am. Chem. Soc. 2011; 133: 19960
- 20a Guo FL, Wang LM, Wang PQ, Yu JJ, Han JW. Asian J. Org. Chem. 2012; 1: 218
- 20b Guo FL, Han JW, Mao S, Li J, Geng X, Yu JJ, Wang LM. RSC Adv. 2013; 3: 6267
- 21 N-Arylation of Naphthalimides with Diaryliodonium Salts; General Procedure: A mixture of 1,8-naphthalimide (0.4 mmol), diaryliodonium salt (0.48 mmol), t-BuOK (2 equiv), CuI (10 mmol%) and toluene (3 mL) was taken in a 10 mL reaction tube and heated at 100 °C for 0.5–2 h under vigorous stirring. After completion of the reaction, as indicated by TLC, the reaction mixture was concentrated under reduced pressure, and the crude compound was purified by chromatography on a silica gel column (EtOAc–petroleum ether) to afford the desired product.
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