Superacid-catalyzed Friedel–Crafts phosphination of 2-hydroxybiphenyls with phosphorus trichloride
Corresponding Author
Takatoshi Ito
Osaka Municipal Technical Research Institute, Osaka, Japan
Correspondence
Takatoshi Ito and Toshinobu Ohno, Osaka Municipal Technical Research Institute, Osaka, Japan.
Emails: [email protected]; [email protected]
Search for more papers by this authorToshiyuki Iwai
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorTakeo Nakai
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorMasatoshi Mihara
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorTakumi Mizuno
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorCorresponding Author
Toshinobu Ohno
Osaka Municipal Technical Research Institute, Osaka, Japan
Correspondence
Takatoshi Ito and Toshinobu Ohno, Osaka Municipal Technical Research Institute, Osaka, Japan.
Emails: [email protected]; [email protected]
Search for more papers by this authorJun-ichi Kobayashi
Marubishi Oil Chemical Co., Ltd, Osaka, Japan
Search for more papers by this authorCorresponding Author
Takatoshi Ito
Osaka Municipal Technical Research Institute, Osaka, Japan
Correspondence
Takatoshi Ito and Toshinobu Ohno, Osaka Municipal Technical Research Institute, Osaka, Japan.
Emails: [email protected]; [email protected]
Search for more papers by this authorToshiyuki Iwai
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorTakeo Nakai
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorMasatoshi Mihara
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorTakumi Mizuno
Osaka Municipal Technical Research Institute, Osaka, Japan
Search for more papers by this authorCorresponding Author
Toshinobu Ohno
Osaka Municipal Technical Research Institute, Osaka, Japan
Correspondence
Takatoshi Ito and Toshinobu Ohno, Osaka Municipal Technical Research Institute, Osaka, Japan.
Emails: [email protected]; [email protected]
Search for more papers by this authorJun-ichi Kobayashi
Marubishi Oil Chemical Co., Ltd, Osaka, Japan
Search for more papers by this authorAbstract
Cyclic phosphorus compounds, 6H-dibenz[c,e][1,2]oxaphosphorin-6-oxide derivatives, were efficiently synthesized by the Friedel–Crafts reaction of 2-hydroxybiphenyls with phosphorus trichloride in the presence of superacids, especially trifluoromethanesulfonic acid (TfOH) as a catalyst. TfOH was investigated for the first time as an effective catalyst for the aromatic phosphination of 2-hydroxybiphenyls.
Supporting Information
| Filename | Description |
|---|---|
| hc21346-sup-0001-FigS1-20.pdfPDF document, 5 MB |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1a) R. L. Fan, L. S. Wang, M. Y. Li, J. Chem. Eng. Data 2008, 53, 228; b) Y. L. Liu, Polymer 2001, 42, 3445; c) W. C. Shan, L. C. Hsuan, Polymer 1999, 40, 4387; d) C. H. Lin, C. S. Wang, Polymer 1869, 2001, 42; e) C. S. Wang, J. Y. Shieh, Polymer 1998, 39, 5819; f) Y. L. Liu, S. H. Tsai, Polymer 2002, 43, 5757.
- 2a) T. Saito, U S Pat 3 1972, 702, 878; b) T. Saito, T. Hirayama, Y. Kohguchi, U S Pat 6 2000, 107, 506; c) H.-J. Kleiner, U S Pat 5 1995, 391, 798 and 5, 1996, 481, 017; d) P. Rathfelder, H. Rieckert, J. Dietrich, U S Pat 5 1998, 821, 376; e) H. Takeuchi, M. Sato, S. Gyobu, U S Pat 6 2001, 245, 880; f) H. J. Kleiner, U S Pat 5 1996, 481, 17.
- 3a) K. A. Salmeia, S. Gaan, Polym. Degrad. Stab. 2015, 113, 119; b) E. A. Chernyshev, V. I. Aksenov, V. V. Ponmarev, S. A. Golubtsov, E. F. Bugerenko, J. Gen. Chem. 1972, 42, 88; c) T. K. Prakasha, R. O. Day, R. R. Holmes, J. Am. Chem. Soc. 1994, 116, 8095; d) S. D. Pastor, J. D. Spivack, L. P. Steinhuebel, Phosphorus Sulfur 1987, 31, 71; e) A. Qureshi, A. S. Hay, J. Chem. Res. (m). 1998, 1601.
- 4H. Tolkmith, J. Org. Chem. 1958, 23, 1682.
- 5a) B. Buchner, L. B. Lockhart Jr, J. Am. Chem. Soc. 1951, 73, 755; b) I. Granoth, Y. Segall, A. Kalir, J. Chem. Soc. Perkin Trans. I 1973, 1972; c) Z. W. Wang, L. S. Wang, Green Chem. 2003, 5, 737.
- 6J. Emsley, D. Hall, The Chemistry of Phosphorus, Harper and Row, London 1976.
- 7F. Siméon, P. A. Jaffrés, D. Villemin, Tetrahedron 1998, 54, 10111.
- 8a) G. A. Olah, G. K. S. Prakash, J. Sommer, Superacids, John Wiley & Sons, New York 1985; b) H. Yamamoto, K. Ishihara, Acid Catalysis in Modern Organic Synthesis, Wiley-VCH, Weinheim 2008.
- 9a) B. Schlummer, J. F. Hartwig, Org. Lett. 2002, 4, 1471; b) T. C. Wabnitz, J. B. Spencer, Org. Lett. 2003, 5, 2141; c) Z. Li, J. Zhang, C. Brouwer, C. G. Yang, N. W. Reich, C. He, Org. Lett. 2006, 8, 4175; d) K. P. Kalbarczyk, S. T. Diver, J. Org. Chem. 2009, 74, 2193.
- 10a) F. Effenberger, F. Buckel, A. H. Maier, J. Schmider, Synthesis 2000, 2000, 1427; b) B. Hulin, M. Koreeda, J. Org. Chem. 1984, 49, 207; c) F. Effenberger, G. Epple, Angew. Chem. Int. Ed. Engl. 1972, 11, 299; d) F. Effenberger, E. Sohn, G. Epple, Chem. Ber. 1983, 116, 1195; e) J. P. Hwang, G. K. S. Prakash, G. A. Olah, Tetrahedron 2000, 56, 7199.
10.1055/s-2000-7102 Google Scholar
- 11D. Nakashima, H. Yamamoto, Org. Lett. 2005, 7, 1251.
- 12N. A. Bumagin, E. V. Luzikova, J. Organomet. Chem. 1997, 532, 271.
- 13A. Buczko, T. Stelzig, L. Bommer, D. Rentsch, M. Heneczkowski, S. Gaan, Polym. Degrad. Stab. 2014, 107, 158.
- 14A. Ciogli, A. D. Cort, F. Gasparrini, F. Lunazzi, L. Mandolini, A. Mazzanti, C. Pasquini, M. Pierini, L. Schiaffino, F. Mihan, J. Org. Chem. 2008, 73, 6108.
