Facile Synthesis of Triarylmethanimine Promoted by a Lewis Acid–Base Pair: Theoretical and Experimental Studies
Yan Liu A , Qiwu Yang A , Dongling Hao A and Wenqin Zhang A B
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Tianjin University, Tianjin 300072, P. R. China.
B Corresponding author. Email: zhangwenqin@tju.edu.cn
Australian Journal of Chemistry 65(10) 1390-1395 https://doi.org/10.1071/CH12090
Submitted: 11 February 2012 Accepted: 27 April 2012 Published: 29 June 2012
Abstract
An efficient method for triarylmethanimine synthesis promoted by a Lewis acid–base pair (AlCl3–Et3N) was designed using mechanistic analysis with the aid of density functional theory. A series of triarylmethanimines were successfully prepared under mild conditions in good to excellent yields with a simple work-up procedure. The promoter, the Lewis acid–base pair (AlCl3–Et3N), is inexpensive, efficient, and shows good functional group tolerance. The experimental results show that the electronic effect played a significant role, i.e. the reactions proceeded smoothly when electron-sufficient arylamines and electron-deficient ketones were used as substrates.
References
[1] H. Schiff, Justus Liebigs Ann. Chem. 1864, 131, 118.| Crossref | GoogleScholarGoogle Scholar |
[2] K. Tsutsui, Y. Shichida, Photochem. Photobiol. Sci. 2010, 9, 1426.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtlGmsLfP&md5=742ee0a21b7ec3854015ddb79385d21fCAS |
[3] Manju, Manju, J. Coord. Chem. 2011, 64, 2130.
| Crossref | GoogleScholarGoogle Scholar |
[4] E. E. Snell, A. E. Braunstein, E. S. Severin, Y. M. Torchinsky, Pyridoxal Catalysis: Enzymes and Model Systems, 1968 (Wiley: New York).
[5] J. A. Joule, G. F. Smith, Heterocyclic Chemistry 1978 (Van Nostrand Reinhold: New York).
[6] P. G. Cozzi, Chem. Soc. Rev. 2004, 33, 410.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXntlWmtLc%3D&md5=0ea2086726ec45e180ca0869b4fe9ab6CAS |
[7] R. Drozdzak, B. Allaert, N. Ledoux, I. Dragutan, V. Dragutan, F. Verpoort, Adv. Synth. Catal. 2005, 347, 1721.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1OgtrvM&md5=0882afd29a971d2423dbe60c6ab12e7bCAS |
[8] P. Schnider, G. Koch, R. Prétôt, G. Wang, F. M. Bohnen, C. Krüger, A. Pfaltz, Chemistry 1997, 3, 887.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXksFyjtLc%3D&md5=828256b4a827ffabd789b783720fea34CAS |
[9] M. Periasamy, G. Srinivas, P. J. Bharathi, J. Org. Chem. 1999, 64, 4204.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXivFChu7o%3D&md5=ff9b99f3121b49a36a037101077b8040CAS |
[10] P.-S. Lai, J. A. Dubland, M. G. Sarwar, M. G. Chudzinski, M. S. Taylor, Tetrahedron 2011, 67, 7586.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFSjtLjL&md5=e6f0a6d6f743fc6baa3b130f90432009CAS |
[11] R. W. Layer, Chem. Rev. 1963, 63, 489.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3sXksFCjs7c%3D&md5=dd7afb5660e343d3c890d9b24ca3d27bCAS |
[12] T. B. Nguyen, H. Bousserouel, Q. Wang, F. Guéritte, Adv. Synth. Catal. 2011, 353, 257.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXitFams7Y%3D&md5=2870e59e2965306c592a21da217ccf0eCAS |
[13] H. H. J. Strain, J. Am. Chem. Soc. 1930, 52, 820.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaA3cXht1egtQ%3D%3D&md5=b0cb92bcba38597de5a303098bf4b5d7CAS |
[14] J. H. Billman, K. M. J. Tai, J. Org. Chem. 1958, 23, 535.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1cXpslOhtw%3D%3D&md5=958ce81414f1de1cfd2195c6ec437cb3CAS |
[15] A. W. Weston, R. J. J. Michaels, J. Am. Chem. Soc. 1951, 73, 1381.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG3MXlt1yksg%3D%3D&md5=a0cbaf0495fd8c441e70d35aa71639f2CAS |
[16] M. Taylor, T. J. Fletcher, J. Org. Chem. 1961, 26, 940.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF3MXht1Cks7o%3D&md5=8aa1d3ed54c72265671118d2bb8e3f6aCAS |
[17] M. Okubo, S. Ueda, Bull. Chem. Soc. Jpn. 1980, 53, 281.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXktVOktLo%3D&md5=c872fc14f9fe975ee5c5015dc9ad9e1dCAS |
[18] J. J. Eisch, R. J. Sanchez, J. Org. Chem. 1986, 51, 1848.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL28XitVKrsbg%3D&md5=464be6689854e5302de39ef3d61c13f3CAS |
[19] M. Higuchi, A. Kimoto, S. Shiki, K. J. Yamamoto, J. Org. Chem. 2000, 65, 5680.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXlsFKmsr4%3D&md5=060cf7fb6930270d69a20a48664c8380CAS |
[20] M. Higuchi, K. Yamamoto, Polym. Adv. Technol. 2002, 13, 765.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpvFWnsA%3D%3D&md5=cdecedbbf81223b46d0e8953b4c5744bCAS |
[21] Y. Ochi, K. Sakurai, K. Azuma, K. Yamamoto, Chemistry 2011, 17, 800.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmtFeqsg%3D%3D&md5=9bf72868078aab4f12a11d952687395fCAS |
[22] G. Mann, J. F. Hartwig, M. S. Driver, C. J. Fernández-Rivas, J. Am. Chem. Soc. 1998, 120, 827.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmvFWmtQ%3D%3D&md5=e3a6eae3c6ca106c81f4ebac2349a84bCAS |
[23] B. E. Love, J. J. Ren, J. Org. Chem. 1993, 58, 5556.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXmsFSiurs%3D&md5=9612b0dcf15f9fc4a246e82eb7845a2cCAS |
[24] J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. J. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXmt12lsLc%3D&md5=157a504aee3f9a3bc786e805cfe2adc7CAS |
[25] J. S. M. Samec, J. E. Bäckvall, Chemistry 2002, 8, 2955.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XltlKqtL8%3D&md5=89fb66862aae9b12bf22ba876ec7baa5CAS |
[26] A. Corma, C. Gonzalez-Arellano, M. Iglesias, M. T. Navarro, F. Sanchez, Chem. Commun. 2008, 6218.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVersbvP&md5=44862700e1d3449b55c7290313c5e548CAS |
[27] S. Liu, Y. Yu, L. S. Liebeskind, Org. Lett. 2007, 9, 1947.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXktlyjurY%3D&md5=c0b2c9af3930e7e707cc6e3cc6c75f66CAS |
[28] Y. Xia, Y. Liang, Y. Chen, M. Wang, L. Jiao, F. Huang, S. Liu, Y. Li, Z.-X. J. Yu, J. Am. Chem. Soc. 2007, 129, 3470.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXitVyiur0%3D&md5=9bda15563980d28f518bdf10549a2411CAS |
[29] Y. Wang, J. Wang, J. Su, F. Huang, L. Jiao, Y. Liang, D. Yang, S. Zhang, P. A. Wender, Z.-X. J. Yu, J. Am. Chem. Soc. 2007, 129, 10060.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotFGnsrs%3D&md5=7d17436c4e742a393bf024f515c60a1dCAS |
[30] Z.-X. Yu, P. H.-Y. Cheong, P. Liu, C. Y. Legault, P. A. Wender, K. N. J. Houk, J. Am. Chem. Soc. 2008, 130, 2378.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsVWiu74%3D&md5=ae73253766e175cf4dd8845a736c6836CAS |
[31] C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXktFWrtbw%3D&md5=1db8a301b13c0d54e6e18228104ee4b7CAS |
[32] A. D. J. Becke, Chem. Phys. 1993, 98, 5648.
| 1:CAS:528:DyaK3sXisVWgtrw%3D&md5=ebe7dc68a8c38908388e1cd8680e671cCAS |
[33] K. J. Fukui, Chem. Phys. 1970, 74, 4161.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXmsFyq&md5=fc49062fe9943138789dacd26c82f4ceCAS |
[34] K. A. K. Ishida, K. Morokuma, A. J. Komornicki, Chem. Phys. 1977, 66, 2153.
| 1:CAS:528:DyaE2sXhslyis70%3D&md5=6f3e06b073400cfeca84906740275d0bCAS |
[35] P. J. Hay, W. R. J. Wadt, Chem. Phys. 1985, 82, 270.
| 1:CAS:528:DyaL2MXhtlyju70%3D&md5=8f9af2da7cf0dae42a6d30822d849529CAS |
[36] P. J. Hay, W. R. J. Wadt, Chem. Phys. 1985, 82, 299.
| 1:CAS:528:DyaL2MXht1SjtLY%3D&md5=af67348f9366b2f8473b62a1688fb58eCAS |
[37] W. R. Wadt, P. J. J. Hay, Chem. Phys. 1985, 82, 284.
| 1:CAS:528:DyaL2MXht1SjtLk%3D&md5=ca678ce4f53b69b7ff8818f361835fb5CAS |
[38] C. E. Check, T. O. Faust, J. M. Bailey, B. J. Wright, T. M. Gilbert, L. S. J. Sunderlin, J. Phys. Chem. A 2001, 105, 8111.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXls1Oru7w%3D&md5=ba609d1d36fae3244f0e1ee32dd52d25CAS |
[39] J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXmsVynurc%3D&md5=7a06382f45d589916740c227ec0fea33CAS |
[40] B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXkvVCgsL4%3D&md5=8f441fd958317f1a7ca98e448900317dCAS |
[41] J. Ho, A. Klamt, M. L. J. Coote, J. Phys. Chem. A 2010, 114, 13442.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsFaktL3I&md5=fef1f0685295310e1a21ead7ad12d20dCAS |
[42] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, 2004 (Wallingford, CT).
