光照条件下链状醚α-碳-氢键官能团化反应研究
收稿日期: 2014-05-29
修回日期: 2014-08-11
网络出版日期: 2014-09-09
基金资助
教育部留学回国人员科研启动基金(No.【45-5】)资助项目.
Photoinduced α-C—H Bond Functionalization of Linear Ethers
Received date: 2014-05-29
Revised date: 2014-08-11
Online published: 2014-09-09
Supported by
Project supported by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry (No.【45-5】).
孙京 , 彭新华 , 郭浩 . 光照条件下链状醚α-碳-氢键官能团化反应研究[J]. 有机化学, 2015 , 35(1) : 246 -250 . DOI: 10.6023/cjoc201405039
A new and effective method for the direct functionalization of ethereal C—H bond was reported. This reaction undergoes smoothly under UV irradiation at room temprature without any additive, which presents a new environmentally friendly protocol to access β-hydroxyl ethers highly selectively. In addition, a possible mechanism of this reaction was proposed.
Key words： photochemistry; C-H functionalization; mechanism; radical reactions; green chemistry
[1] (a) Goldberg, K. I.; Goldman, A. S. Activation and Functionalization of C-H Bonds, American Chemical Society, Washington, DC, 2004. (b) Dyker, G. Handbook of C-H Transformations: Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2005. (c) Yu, J. Q.; Shi, Z. C—H Activation, Springer-Verlag, Berlin, 2010.
[2] (a) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633. (b) Yu, S.; Ma, S. Chin. J. Org. Chem. 2002, 22, 307 (in Chinese). (余世超, 麻生明, 有机化学, 2002, 22, 307.) (c) D?az-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379. (d) Chen, X.; Engle, K. M.; Wang, D. H.; Yu, J. Q. Angew. Chem., Int. Ed. 2009, 48, 5094. (e) Giri, R.; Shi, B. F.; Engle, K. M.; Maugel, N.; Yu, J. Q. Chem. Soc. Rev. 2009, 38, 3242. (f) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147. (g) McMurray, L.; O'Hara, F.; Gaunt, M. J. Chem. Soc. Rev. 2011, 40, 1885. (h) Boorman, T. C.; Larrosa, I. Chem. Soc. Rev. 2011, 40, 1910. (i) Lewis, J. C.; Coelho, P. S.; Arnold, F. H. Chem. Soc. Rev. 2011, 40, 2003. (j) Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864. (k) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679 (in Chinese). (潘菲, 施章杰, 化学学报, 2012, 70, 1679.) (l) Liu, W.; Bi, Y. Chin. J. Org. Chem. 2012, 32, 1041 (in Chinese). (刘伟, 毕艳兰, 有机化学, 2012, 32, 1041.)
[3] (a) Chatani, N.; Asaumi, T.; Yorimitsu, S.; Ikeda, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 2001, 123, 10935. (b) Murahashi, S. I.; Nakae, T.; Terai, H.; Komya, N. J. Am. Chem. Soc. 2008, 130, 11005. (c) Li, Z.; Yu, R.; Li, H. Angew. Chem., Int. Ed. 2008, 47, 7497. (d) Kubiak, R.; Prochnow, I.; Doye, S. Angew. Chem., Int. Ed. 2009, 48, 1153. (e) Zhang, S.; Tu, Y.; Fan, C.; Zhang, F.; Shi, L. Angew. Chem., Int. Ed. 2009, 48, 8761. (f) Li, F.; Jiang, T.; Cai, H.; Wang, G. Chin. J. Chem. 2012, 30, 2041. (g) Ma, Y.; Li, W.; Yu, B. Acta Chim. Sinica 2013, 71, 541 (in Chinese). (马玉勇, 李薇, 俞飚, 化学学报, 2012, 71, 541.)
[4] (a) Bertrand, S.; Hoffmann, N.; Pete, J. P. Eur. J. Org. Chem. 2000, 2227. (b) Bauer, A.; Westkämper, F.; Grimme, S.; Bach, T. Nature 2005, 436, 1139.
[5] For ethereal C—H bond functionalization, see: (a) Yoshimitsu, T.; Tsunoda, M.; Nagaoka, H. Chem. Commun. 1999, 1745. (b) Mosca, R.; Fagnoni, M.; Mella, M.; Albini, A. Tetrahedron 2001, 57, 10391. (c) Yamada, K.; Fujihara, H.; Yamamoto, Y.; Miwa, Y.; Taga, T.; Tomioka, K. Org. Lett. 2002, 4, 3509. (d) Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2003, 68, 625. (e) Yamada, K.; Yamamoto, Y.; Tomioka, K. Org. Lett. 2003, 5, 1797. (f) Fernández, M.; Alonso, R. Org. Lett. 2003, 5, 2462. (g) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2003, 68, 7548. (h) Yamamoto, Y.; Yamada, K.; Tomioka, K. Tetrahedron Lett. 2004, 45, 795. (i) Yamada, K.; Yamamoto, Y.; Maekawa, M.; Tomioka, K. J. Org. Chem. 2004, 69, 1531. (j) Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2005, 70, 2342. (k) Akindele, T.; Yamamoto, Y.; Maekawa, M.; Umeki, H.; Yamada, K.; Tomioka, K. Org. Lett. 2006, 8, 5729. (l) Shikanai, D.; Murase, H.; Hata, T.; Urabe, H. J. Am. Chem. Soc. 2009, 131, 3166. (m) Jurberg, I. D.; Odabachian, Y.; Gagosz, F. J. Am. Chem. Soc. 2010, 132, 3543.
[6] Hao, X.; Liu, C.; Liu, C.; Chen, Y.; Zhao, X.; Song, M.; Qian, R.; Guo, H. Tetrahedron Lett. 2013, 54, 6964.
[7] Yoshida, Z.; Kimura, M. Tetrahedron 1975, 31, 221.
[8] The structure of product 3 was determined by 1H NMR analysis according to corresponding literature reported data[6,9,10].
[9] Yoshimitsu, T.; Arano, Y.; Nagaoka, H. J. Org. Chem. 2005, 70, 2342.
[10] Yuan, Z.; Li, X. Chin. J. Magn. Res. 2003, 20, 307 (in Chinese). (原忠, 李铣, 波谱学杂志, 2003, 20, 307.)
[11] Bertrand, S.; Hoffmann, N.; Humbel, S.; Pete, J. P. J. Org. Chem. 2000, 65, 8690.
[12] Eisch, J. J.; Galle, J. E.; Piotrowski, A.; Tsai, M. J. Org. Chem. 1982, 47, 5051.
/
| 〈 |
|
〉 |
