铜催化烯酸和苯硫酚类化合物的氧硫化反应研究:合成硫化内酯类化合物
收稿日期: 2017-02-27
修回日期: 2017-04-01
网络出版日期: 2017-04-18
基金资助
河北省自然科学基金重点(No.B2016201031)、河北省高等学校高层次人才科学研究(No.GCC2014014)、河北省自然科学基金青年(No.B2017201041)资助项目.
Copper-Catalyzed Oxysulfenylation of Alkenoic Acids with Benzenethiols: A Strategy to Construct Sulfenylated Lactones
Received date: 2017-02-27
Revised date: 2017-04-01
Online published: 2017-04-18
Supported by
Project supported by the Hebei Province Science, foundation for Key Program (No. B2016201031), the Hebei Province Higher School Science, foundation for High-level Personnel (No. GCC2014014), and the Hebei Province Science, foundation for Youths (No. B2017201041).
陈漫漫 , 王力竞 , 李玮 . 铜催化烯酸和苯硫酚类化合物的氧硫化反应研究:合成硫化内酯类化合物[J]. 有机化学, 2017 , 37(5) : 1173 -1180 . DOI: 10.6023/cjoc201702042
An efficient copper-catalyzed oxysulfenylation of alkenoic acids with benzenethiols via radical pathway was developed. The reactions are easy to be conducted under mild conditions and form a broad range of sulfenylated lactones.
Key words: copper-catalyzed; benzenethiols; radical reaction; oxysulfenylation; lactones
[1] (a) Page, P. C. B. Organosulfur Chemistry I. In Topics in Current Chemistry, Springer, Berlin, 1999, Vol. 204.
(b) Page, P. C. B. Organosulfur Chemistry II. In Topics in Current Chemistry, Springer, Berlin, 1999, Vol. 205.
(c) Jeppesen, J. O.; Nielsen, M. B.; Becher, J. Chem. Rev. 2004, 104, 5115.
(d) Secrist, J. A., III; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem. 1991, 34, 2361.
(e) Bagli, J. F.; Mackay, W. D.; Ferdinandi, E. F. J. Med. Chem. 1976, 19, 876.
(f) Bichler, P.; Love, J. In Topics of Organometallic Chemistry, Ed.: Vigalok, A., Springer, Heidelberg, 2010, Vol. 31, p. 39.
(g) McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239.
(h) Zyk, N. V.; Beloglazkina, E. K.; Belova, M. A.; Dubinina, N. S. Russ. Chem. Rev. 2003, 72, 769.
[2] (a) Matsumoto, K.; Sugiyama, H. Acc. Chem. Res. 2002, 35, 915.
(b) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596.
(c) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X. Chem. Soc. Rev. 2015, 44, 291.
(d) Li, H.; Wang, Z.; Deng, W. Chin. J. Org. Chem. 2016, 36, 2419 (in Chinese). (李红亮, 王正林, 邓卫平, 有机化学, 2016, 36, 2419.)
(e) Zhang, B.; Kang, Y.; Shi, R. Chin. J. Org. Chem. 2016, 36, 1814 (in Chinese). (张变香, 亢永强, 史瑞雪, 有机化学, 2016, 36, 1814.)
(f) Wang, D.; Zhang, R.; Lin, S.; Deng, R.; Yan, Z. Chin. J. Org. Chem. 2016, 36, 2757 (in Chinese). (王丁意, 张荣兴, 林森, 邓瑞红, 严兆华, 有机化学, 2016, 36, 2757.)
(g) Wang, J.; Wu, J.; Tian, W. Chin. J. Chem. 2015, 33, 632.
(h) Hu, D.; Bai, F.; Liu, Y.; Wan, J.-P. Chin. J. Chem. 2016, 34, 1053.
(i) Yu, H.; Zhang, Y. Chin. J. Chem. 2016, 34, 359.
[3] (a) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Kato, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
(b) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 13.
[4] (a) Mann, G.; Baranano, D.; Hartwig, J. F.; Rheingold, A. L.; Guzei, I. A. J. Am. Chem. Soc. 1998, 120, 9205.
(b) Murata, M.; Buchwald, S. L. Tetrahedron 2004, 60, 7397.
(c) Itoh, T.; Mase, T. Org. Lett. 2004, 6, 4587.
(d) Fernandez-Rodroeguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
(e) Itoh, T.; Mase, T. Org. Lett., 2007, 9, 3687.
(f) Lee, J. Y.; Lee, P. H. J. Org. Chem. 2008, 73, 7413.
(g) Dahl, T.; Tornoe, C. W.; Bang-Andersen, B.; Nielsen, P.; Jorgensen, M. Angew. Chem., Int. Ed. 2008, 47, 1726.
(h) Eichman, C. C.; Stambuli, J. P. J. Org. Chem. 2009, 74, 4005.
[5] (a) Bates, C. G.; Gujadhur, R. K.; Venkataraman, D. Org. Lett. 2002, 4, 2803.
(b) Jammi, S.; Sakthivel, S.; Rout, L.; Mukherjee, T.; Mandal, S.; Mitra, R.; Saha, P.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 1971.
(c) Larsson, P.-F.; Correa, A.; Carril, M.; Norrby, P.-O.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 5691.
(d) Xu, H.-J.; Zhao, Y.-Q.; Feng, T.; Feng, Y.-S. J. Org. Chem. 2012, 77, 2878.
(e) Kumar, S.; Engman, L. J. Org. Chem. 2006, 71, 5400.
(f) Taniguchi, N. J. Org. Chem. 2007, 72, 1241.
(g) Zhang, S.; Qian, P.; Zhang, M.; Hu, M.; Cheng, J. J. Org. Chem. 2010, 75, 6732.
(h) Hao, W.; Zeng, J.; Cai, M. Chem. Commun. 2014, 50, 11686.
[6] (a) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., Int. Ed. 2008, 47, 2880.
(b) Wu, J.-R.; Lin, C.-H.; Lee, C.-F. Chem. Commun. 2009, 4450.
(c) Lin, Y.-Y.; Wang, Y.-J.; Lin, C.-H.; Cheng, J.-H.; Lee, C.-F. J. Org. Chem. 2012, 77, 6100.
(d) Wang, H.; Wang, L.; Shang, J.; Li, X.; Wang, H.; Gui, J.; Lei, A. Chem. Commun. 2012, 48, 76.
[7] (a) Arisawa, M.; Ichikawa, T.; Yamaguchi, M. Org. Lett. 2012, 14, 5318.
(b) Arisawa, M.; Suzuki, T.; Ishikawa, T.; Yamaguchi, M. J. Am. Chem. Soc. 2008, 130, 12214.
(c) Ajiki, K.; Hirano, M.; Tanaka, K. Org. Lett. 2005, 7, 4193.
[8] (a) Patai, S. The Chemistry of Double-Bonded Functional Groups, Wiley, Chichester, 1997.
(b) Wang, F.; Qi, X.; Liang, Z.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2014, 53, 1881.
(c) Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202.
(d) Bunescu, A.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2015, 54, 3132.
(e) Liu, X.; Xiong, F.; Huang, X.; Xu, L.; Li, P.; Wu, X. Angew. Chem., Int. Ed. 2013, 52, 6962.
(f) Chen, J.-R.; Yu, X.-Y.; Xiao, W.-J. Synthesis 2015, 47, 604.
(g) Song, R.-J.; Liu, Y.; Xie, Y.-X.; Li, J.-H. Synthesis 2015, 47, 1195.
[9] (a) Hudlicky, M. Oxidations in Organic Chemistry, ACS Monograph Series 186, American Chemical Society, Washington, DC, 1990, p. 174.
(b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed., Ed.: Ojima, I., Wiley-VCH, New York, Weinheim, 2000, p. 357.
[10] (a) Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 8069.
(b) Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2012, 134, 12462.
(c) Zhu, R.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 12655.
[11] Gao, Y.; Gao, Y.; Tang, X.; Peng, J.; Hu, M.; Wu, W.; Jiang, H. Org. Lett. 2016, 18, 1158.
[12] (a) Samii, Z. K. M. Abd El; Ashmawy, M. I. Al; Mellor, J. M. Tetrahedron Lett. 1987, 28, 1949.
(b) Vas'kevich, A. I.; Tsizorik, N. M.; Rusanov, E. B.; Staninets, V. I.; Vovk M. V. Russ. J. Org. Chem. 2012, 48, 193.
[13] Wang, L.-J.; Chen, M.; Qi, L.; Xu, Z.; Li, W. Chem. Commun. 2017, 53, 2056.
[14] (a) Huo, C.; Wang, Y.; Yuan, Y.; Chen, F.; Tang, J. Chem. Commun. 2016, 52, 7233.
(b) Huang, Z.; Zhang, D.; Qi, X.; Yan, Z.; Wang, M.; Yan, H.; Lei, A. Org. Lett., 2016, 18, 2351.
[15] Kang, Y.-B. Chen, X.-M. Yao, C.-Z. Ning, X.-S. Chem. Commun. 2016, 52, 6193.
[16] (a) Samii, Z. K. M. Abel El.; Ashmawy, M. I Al.; Mellor, J. M. Tetrahedron Lett. 1986, 27, 5293.
(b) Tiecco, M.; Tingoli, M.; Testaferri, L.; Balducci, R. J. Org. Chem. 1992, 57, 4025.
/
| 〈 |
|
〉 |