Facile New Syntheses of Substituted Benzhydryl Derivatives Using Trichloroacetimidate C-C Bond Formation Method
Science Journal of Chemistry
Volume 2, Issue 5, October 2014, Pages: 38-43
Received: Nov. 17, 2014; Accepted: Nov. 26, 2014; Published: Dec. 5, 2014
Views 2413      Downloads 140
Author
Walid Fathalla, Department of Mathematics and Physics, Faculty of Engineering, Port-Said University, Port Said, Egypt
Article Tools
Follow on us
Abstract
An improved syntheses of substituted benzhydryl derivatives has been developed. This facile two-step procedure involves C-C bond formation from O-diphenylmethyltrichloroacetimidate and C-nucleophiles in the presence of TMSOTf. The C-nucleophiles include arenes, alkenes, alkene silylated C-nucleophiles and trimethylsiloxy alkenes to give a series substituted benzhydryl derivatives in excellent yields.
Keywords
Trichloroacetimidate Method, C-C Bond Formation, C-Nucleophiles, Bezhydryl Derivatives
To cite this article
Walid Fathalla, Facile New Syntheses of Substituted Benzhydryl Derivatives Using Trichloroacetimidate C-C Bond Formation Method, Science Journal of Chemistry. Vol. 2, No. 5, 2014, pp. 38-43. doi: 10.11648/j.sjc.20140205.11
References
[1]
Garnett, W. R. (1986). Am Pharm., 26, 35-40.
[2]
Ashimori, A., Uchida, T., Ohtaki, Y., Tanaka, M., Ohe, K., Fukaya, C., Watanabe, M., Kagitani, M., Yokoyama, K. (1991). Chem. Pharm. Bull., 39, 108-111.
[3]
Glushkov, R. G., Juzhakov, S. D., Fominova, O. S., Sazonova, N. M., Dolginova, E. M., Shorr, V. A., Borovkov, M. V. &Asnina, V. V. (2010). U.S. Patent No. 0168425A1. Washington, D.C.: U.S. Patent and Trademark Office.
[4]
Domino, E. F. (1999). Psychosomatic Medicine 61, 591-598.
[5]
Kim, Y. S., Shin, Y. K., Lee, C., Song, J. (2000). Brain Research 881, 190-198.
[6]
King, A. O., Okukado, N., Negishi, E. (1977). J. Chem. Soc. Chem. Commun. (19), 683-691.
[7]
Miyaura, N., Yamada, K., Suzuki, A. (1979). Tetrahed. Lett. 20 (36), 3437–3440.
[8]
Drahl, C. (2010). Chem. and Eng. News 88 (22), 31–33.
[9]
Zhang, L., Sun, J., Kozmin, S. A. (2006). Tetrahedron 62, 11371–11380.
[10]
Kotsuki, H., Ohishi, T., Inoue, M., Kojima, T. (1999). Synthesis 603–606.
[11]
Ali, I. A. I. (2014). Monatsh. Chem. 145, 803-810.
[12]
Shirakawa, S., Kobayashi, S. (2006). Org. Lett. 8, 4939–4942.
[13]
Schmidt, R. R., Kinzy, W. (1994). Adv. Carbohydr. Chem. Biochem.50, 21-123.
[14]
Schmidt, R. R., Jung, K.-H. (1997). In Preparative Carbohydrate Chemistry, S. Hannessian, Ed. Marcel Dekker, Inc. New York, 283-312.
[15]
Ali, I. A. I., Abdel-Rahman, A. A-H., El-Ashry, E. S. H., Schmidt, R. R. (2003). Eur. J. Org. Chem. 4121-4131.
[16]
Ali, I. A. I., Abdel-Rahman, A. A-H, El-Ashry, E. S. H., Schmidt, R. R. (2003). Synthesis (7), 1065-1070.
[17]
Ali, I. A. I., Fathalla,W. (2009). ARKIVOC (xiii) 193-199.
[18]
Ali, I. A. I., Fathalla,W. (2013). Curr. Org. Chem. 17, 1903-1909.
[19]
Cramer, F., Henrich, N. (1961). Chem. Ber. 94, 976-989.
[20]
Norris, J. F., Young, R. C. (1924). J. Am. Chem. Soc., 24, 2580-2583.
[21]
Burton, H., Cheeseman G. W. H. (1953). J. Chem Soc., 832-837.
[22]
Liu, C., Li, M., Yang, C., Tian, S. (2009). Chem. Eur. J. 15, 793-797.
[23]
Les Bras, J., Muzart, J. (2007). Tetrahedron 63, 7942-7948.
[24]
Kauffmann, H., Pannwitz, P. (1912). Chem. Ber. 45, 766-776.
[25]
Sandip, N., Shukla, P., Choudhary, M. (2011). Synlett, 1585-1591.
[26]
Szeki, T. (1923). Chem. Ber. 56B, 2464-2468.
[27]
Darbeau, R. W., White, E. H. (1997). J. Org. Chem. 62, 8091-8094.
[28]
MacKnight, E., McClelland R. A. (1996). Can. J. Chern. 74, 2518-2527.
[29]
Burekhalter, J. H., Johnson, S. M. (1951). J. Am. Chem. Soc. 73, 4827-4829.
[30]
Marcuzzi, F., Melloni, G., Modena, G. (1979). J. Org. Chem. 44, 3022-3028.
[31]
Yamamura, K. (1978). J. Org. Chem. 43, 724-727.
[32]
Bond, J., Wright, G. (1950). J. Am. Chem. Soc. 72, 1023-1024.
[33]
Devinean, A. Pousse, G., Taillier, C., Blanchet, J., Rouden, J., Dalla, V. (2010). Adv. Synth. Cat. 352, 2881-2886.
[34]
Winthrop, S. O., Humber, L. G. (1961). J. Org. Chem. 26, 2834-2836.
[35]
Ozaki, S., Yoshinaga, H., Matsui, E., Adachi, M. (2001). J. Org. Chem. 66, 2503-2505.
[36]
Walborski, H. M., Pitt, C. G. (1962). J. Am. Chem. Soc., 84, 4831-4838.
[37]
Mayr, H., Pock, R. (1986). Tetrahedron, 42, 4211-4214.
[38]
Grovenstein,. E. & Cottingham, A. B. (1977). J. Am. Chem. Soc. 73, 1881-1889.
ADDRESS
Science Publishing Group
1 Rockefeller Plaza,
10th and 11th Floors,
New York, NY 10020
U.S.A.
Tel: (001)347-983-5186