234
Views
5
CrossRef citations to date
0
Altmetric
Original Articles

Convenient synthesis of α-diarylmethylphosphonates by HOTf catalyzed Friedel-Crafts arylation of α-aryl α-hydroxyphosphonates

, , &
Pages 168-177 | Received 18 Jul 2017, Accepted 13 Oct 2017, Published online: 13 Nov 2017

References

  • Jackson, E. R., Dowd, C. S. Curr. Top. Med. Chem. 2012, 12, 706-728. (b) Montel. S., Midrier, C., Volle, J.-N., Braun, R., Haaf, K., Willms, L., Pirat, J.-L., Virieux, D. Eur. J. Org. Chem. 2012, 17, 3237-3248.
  • (a) Wu, D., Niu, J.-Q., Ding, Y.-H., Wu, X.-Y., Zhong, B.-H., Feng, X.-W. Med. Chem. Res. 2012, 21, 1179-1187. (b) Romanenko, V. D., Kukhar, V. P. Beilstein J. Org. Chem. 2013, 9, 991-1001. (c) Alexandre, F., Amador, A., Bot, S., Caillet, C., Convard, T., Jakubik, J., Musiu, C., Poddesu, B., Vargiu, L., Liuzzi, M., et al. Med. Chem. 2011, 54, 392-395.
  • (a) Walawalkar, M. G., Roesky, H. W., Murugavel, R. Acc. Chem. Res. 1999, 32, 117-126. (b) Baumgartner, T., Réau, R. Chem. Rev. 2006, 106, 4681-4727. (c) Shimizu, G. K. H., Vaidhyanathan, R., Taylor, J. M. Chem. Soc. Rev. 2009, 38, 1430-1449.
  • (a) Lagasse, F., Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315-324. (b) Lam, F. L., Kwong, F. Y., Chan, A. S. C. Top. Organomet. Chem. 2011, 36, 29-36. (c) Lühr, S., Holz, J., Börner, A. Chem. Cat. Chem. 2011, 3, 1708-1730.
  • (a) Boutagy, J., Thomas, R. Chem. Rev. 1974, 74, 87-99. (b) Bisceglia, J. A., Orelli, L. R. Curr. Org. Chem. 2012, 16, 2206-2230. (c) Bisceglia, J. A., Orelli, L. R. Curr. Org. Chem. 2015, 19, 744-775.
  • Younes, S., Baziard-Mouysset, G., de Saqui-Sannes, G., Stigliani, J. L., Payard, M., Bonnafous, R., Tisne-Versailles, J. Eur. J. Med. Chem. 1993, 28, 943-948. doi:10.1016/0223-5234(93)90049-K.
  • Motoyoshiya, J., Ikeda, T., Tsuboi, S., Kusaura, T., Takeuchi, Y., Hayashi, S., Yoshioka, S., Takaguchi, Y., Aoyama, H. J. Org. Chem. 2003, 68, 5950-5955. doi:10.1021/jo030046l.
  • (a) Bhattacharya, A. K., Thyagarajan, G. Chem. Rev. 1981, 81, 415-430. (b) Michaelis, A., Kaehne, R. Ber. Dtsch. Chem. Ges. 1898, 31, 1048-1055. (c) Arbuzov, B. A. Pure Appl. Chem. 1964, 9, 307-336. (d) Rajeshwaran, G. G., Nandakumar, M., Sureshbabu, R., Mohanakrishnan, A. K. Org. Lett. 2011, 13, 1270-1273. (e) Demmer, C. S, Krogsgaard-Larsen, N., Bunch, L. Chem. Rev. 2011, 111, 7981-8006.
  • Montel, S., Raffier, L., He, Y., Walsh, P. J. Org. Lett. 2014, 16, 1446-1449. doi:10.1021/ol5002413.
  • (a) Arde, P., Anand, R. V. Org. Biomol. Chem. 2016, 14, 5550-5554. (b) Molleti, N., Kang, J. Y. Org. Lett. 2017, 19, 958-961. (c) Chen, Z.-S., Zhou, Z.-Z., Hua, H.-L., Duan, X.-H., Luo, J.-Y., Wang, J., Zhou, P.-X., Liang, Y.-M. Tetrahedron. 2013, 69, 1065-1068. (d) Zhou, Y., Zhang, Y., Wang, J., Chin., J. Chem. 2017, 35, 621-627.
  • (a) Rueping, M., Nachtsheim, B. J., Beilstein J. Org. Chem. 2010, 6, No. 6 doi:10.3762/bjoc.6.6. (b) Dryzhakov, M., Richmond, E., Moran, J. Synthesis. 2016, 48, 935-959.
  • (a) Pallikonda, G., Chakravarty, M. RSC Adv. 2013, 3, 20503-20511. (b) Anitha, M., Kotikalapudi, R., Kumaraswamy, K. C. J. Chem. Sci. 2015, 127, 1465-1475.
  • (a) Trost, B. M. Science. 1991, 254, 1471-1477. (b) Wender, P. A. Chem. Rev. 1996, 96, 1-2. (c) Sheldon, R. A. Pure Appl. Chem. 2000, 72, 1233-1246. (d) Anastas, P., Eghbali, N. Chem. Soc. Rev. 2010, 39, 301-312.
  • Generally, α-aryl α-hydroxyphosphonates 1 could be easily synthesized by the Pudovik reaction. (a) Abell, J. P., Yamamoto, H. J. Am. Chem. Soc. 2008, 130, 10521-10523. (b) Suyama, K., Sakai, Y., Matsumoto, K., Saito, B., Katsuki, T. Angew. Chem. Int. Ed. 2010, 49, 797-799. (c) Kulkarni, M. A., Lad, U. P., Desai, U. V., Mitragotri, S. D., Wadgaonkar, P. P. C. R. Chimie. 2013, 16, 148-152. (d) Liu, C., Zhang, Y., Qian, Q., Yuan, D., Yao, Y. Org. Lett. 2014, 16, 6172-6175.
  • Pallikonda, G., Chakravarty, M. Eur. J. Org. Chem. 2013, 944-951. doi:10.1002/ejoc.201201352.
  • (a) Shirakawa, S., Kobayashi, S. Org. Lett. 2007, 9, 311-314. (b) Sanz, R., Miguel, D., Álvarez-Gutiérrez, J. M., Rodríguez, F. Synlett. 2008, 975-978. (c) McCubbin, J. A., Hosseini, H., Krokhin, O. V. J. Org. Chem. 2010, 75, 959-962. (d) Rueping, M., Nachtsheim, B. J., Ieawsuwan, W. Adv. Synth. Catal. 2006, 348, 1033-1037. (e) Wu, Y.-C., Li, H.-J., Liu, L., Demoulin, N., Liu, Z., Wang, D., Chen, Y.-J. Adv. Synth. Catal. 2011, 353, 907-912. (f) Chen, L., Yin, X.-P., Wang, C.-H., Zhou, J. Org. Biomol. Chem. 2014, 12, 6033-6048. also see ref. 11a.
  • For transformations based on vinylogous iminium intermediates, see: (a) Wang, S.-Y., Ji, S.-J. Tetrahedron. 2006, 62, 1527-1535. (b) Rueping, M., Nachtsheim, B. J., Moreth, S. A., Bolte, M. Angew. Chem. Int. Ed. 2008, 47, 593-596. (c) Wang, D.-S., Tang, J., Zhou, Y.-G., Chen, M.-W., Yu, C.-B., Duan, Y., Jiang, G.-F. Chem. Sci. 2011, 2, 803-806. (d) Moghadam, K. R., Kiasaraie, M. S., Amlashi, H. T. Tetrahedron. 2010, 66, 2316-2321. (e) Ahadi, S., Moafi, L., Feiz, A., Bazgir, A. Tetrahedron. 2011, 67, 3954-3958.
  • (a) Chen, L., Zhou, J. Chem. Asian. J. 2012, 7, 2510-2515. (b) Chen, L., Zhou, F., Shi, T.-D. J. Zhou, J. Org. Chem. 2012, 77, 4354-4362.
  • For a comprehensive review, see: Dalpozzo, R., Bartoli, G., Sambri, L., Melchiorre, P. Chem. Rev. 2010, 110, 3501-3551. doi:10.1021/cr9003488.
  • Luo, S., Zhu, L., Talukdar, A., Zhang, G., Mi, X., Cheng, J.-P., Wang, P. G. Mini-Rev. Org. Chem. 2005, 2, 177-202. doi:10.2174/1570193053544472.
  • (a) Akiyama, T. Chem. Rev. 2007, 107, 5744-5748. (b) Cheon, C. H., Yamamoto, H. Chem. Commun. 2011, 47, 3043-3056.
  • We also tried the reaction of simple benzene and other arenes with electronwithdrawing group such as bromobenzene, chlorobenzene with α-hydroxyphosphonate 1a, but found most of 1a underwent the retro-Pudovik reaction under the strong acid conditions. Meanwhile, due to the low nucleophilicity of these arenes (benzene, bromobenzene and chlorobenzene), the Friedel-Crafts arylation between 1a and these arenes could hardly proceed, which resulted in no desired arylated product detected.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.