An Efficient Synthesis of 2-Vinyl Furans/Thiophenes: Oxidative Heck Coupling under High-Speed Ball-Milling Conditions

doi:10.6023/cjoc201612047

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (6): 1473-1478.DOI: 10.6023/cjoc201612047 Previous Articles Next Articles

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一种2-烯基呋喃/噻吩的高效合成方法：高速球磨条件下的氧化Heck偶联反应

贾侃彦^a, 江之江^b, 俞静波^b, 洪子坤^a, 苏为科^a,b

a. 浙江工业大学药学院杭州 310014;
b. 浙江工业大学长三角绿色制药协同创新中心杭州 310014

收稿日期:2016-12-18 修回日期:2017-02-08 发布日期:2017-02-15
通讯作者: 苏为科 E-mail:pharmlab@zjut.edu.cn
基金资助:
国家重点基础研究发展计划（No.2014CB460608）和国家自然科学基金（Nos.21406201，21276237）资助项目.

An Efficient Synthesis of 2-Vinyl Furans/Thiophenes: Oxidative Heck Coupling under High-Speed Ball-Milling Conditions

Jia Kanyan^a, Jiang Zhijiang^b, Yu Jingbo^b, Hong Zikun^a, Su Weike^a,b

a. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014;
b. Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, Zhejiang University of Technology, Hangzhou 310014

Received:2016-12-18 Revised:2017-02-08 Published:2017-02-15
Contact: 10.6023/cjoc201612047 E-mail:pharmlab@zjut.edu.cn
Supported by:
Project supported by the Special Program for Key Basic Research of the Ministry of Science and Technology of China (No. 2014CB460608) and the National Natural Science Foundation of China (Nos. 21406201, 21276237).

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Jia Kanyan, Jiang Zhijiang, Yu Jingbo, Hong Zikun, Su Weike. An Efficient Synthesis of 2-Vinyl Furans/Thiophenes: Oxidative Heck Coupling under High-Speed Ball-Milling Conditions[J]. Chin. J. Org. Chem., 2017, 37(6): 1473-1478.

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[1] (a) Paquette, L. A.; Efremov, I. J. Am. Chem. Soc. 2001, 123, 4492.
(b) Reiter, M.; Torssell, S.; Lee, S.; MacMillan, D. W. C. Chem. Sci. 2010, 1, 37.
(c) Pisani, L.; Barletta, M.; Soto-Otero, R.; Nicolotti, O.; Mendez-Alvarez, E.; Catto, M.; Introcaso, A.; Stefanachi, A.; Cellamare, S.; Altomare, C.; Carotti, A. J. Med. Chem. 2013, 56, 2651.
(d) Simonetti, S. O.; Larghi, E. L.; Bracca, A. B. J.; Kaufman, T. S. Nat. Prod. Rep. 2013, 30, 941.
[2] (a) Berthiol, F.; Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2002, 43, 5625.
(b) Pankova, A. S.; Sorokina, M. V.; Kuznetsov, M. A. Tetrahedron Lett. 2015, 56, 5381.
(c) Škorica, I.; Flegara, I.; Marinic, Z.; Šindler-Kulyk, M. Tetrahedron 2006, 62, 7396.
(d) Liu, W.-D.; Wang, D.-F.; Duan, Y.-J.; Zhang, Y.-H.; Bian, F.-L. Tetrahedron Lett. 2015, 56, 1784.
[3] (a) Jia, C.-G.; Lu, W.-J.; Kitamura, T.; Fujiwara, Y. Org. Lett. 1999, 1, 2097.
(b) Yokota, T.; Tani, M.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2003, 125, 1476.
(c) Tani, M.; Sakaguchi, S.; Ishii, Y. J. Org. Chem. 2004, 69, 1221.
(d) Zhao, J.; Huang, L.; Cheng, K.; Zhang, Y. Tetrahedron Lett. 2009, 50, 2758.
(e) Su, Y.-J.; Jiao, N. Curr. Org. Chem. 2011, 15, 3362
[4] (a) Thiery, E.; Harakat, D.; Le Bras, J.; Muzart, J. Organometallics 2008, 27, 3996.
(b) Aouf, C.; Thiery, E.; Le Bras, J.; Muzart, J. Org. Lett. 2009, 11, 4096.
(c) Vasseur, A.; Harakat, D.; Muzart, J.; Le Bras, J. J. Org. Chem. 2012, 77, 5751.
(d) Vasseur, A.; Harakat, D.; Muzart, J.; Le Bras, J. Adv. Synth. Catal. 2013, 355, 59.
[5] (a) Wang, G.-W. Chem. Soc. Rev. 2013, 42, 7668.
(b) Hernández, J. G.; Frišcic, T. Tetrahedron Lett. 2015, 56, 4253.
[6] (a) Hermann, G. N.; Becker, P.; Bolm, C. Angew. Chem., Int. Ed. 2015, 54, 7414.
(b) Hernández, J. G.; Bolm, C. Chem. Commun. 2015, 51, 12582.
(c) Hermann, G. N.; Becker, P.; Bolm, C. Angew. Chem., Int. Ed. 2016, 55, 3781.
(d) Lou, S.-J.; Mao, Y.-J.; Xu, D.-Q.; He, J.-Q.; Chen, Q.; Xu, Z.-Y. ACS Catal. 2016, 6, 3890.
[7] Jia, K.-Y.; Yu, J.-B.; Jiang, Z.-J.; Su. W.-K. J. Org. Chem. 2016, 81, 6049.
[8] Cornell, C. N.; Sigman, M. S. Inorg. Chem. 2007, 46, 1903.
[9] Hashmi, A. S. K.; Hamzic, M.; Rominger, F.; Bats, J. W. Chem. Eur. J. 2009, 15, 13318.
[10] Shearouse, W. C.; Mac, J. Green Chem. 2012, 14, 2771.
[11] Maillard, J.; Langlois, M.; Tri, V. V.; Guillonneau, C.; Legeai, J.; Benharkate, M.; Blozovski, M. Eur. J. Med. Chem. 1983, 18, 353.
[12] Vasseur, A.; Muzart, J.; Le Bras, J. Chem. Eur. J. 2011, 17, 12556.
[13] Tominaga, Y.; Tedjamulia, M. L.; Castle, R. N.; Lee, M. L. J. Heterocycl. Chem. 1983, 20, 487.
[14] Hyotanishi, M.; Isomura, Y.; Yamamoto, H.; Kawasaki, H.; Obora, Y. Chem. Commun. 2011, 47, 5750.
[15] Matsunaga, N.; Kaku, T.; Itoh, F.; Tanaka, T.; Hara, T.; Miki, H.; Iwasaki, M.; Aono, T.; Yamaoka, M.; Kusaka, M. Bioorg. Med. Chem. 2004, 12, 2251.
[16] Miller, R. E.; Nord, F. F. J. Org. Chem. 1950, 15, 89.

一种2-烯基呋喃/噻吩的高效合成方法：高速球磨条件下的氧化Heck偶联反应

An Efficient Synthesis of 2-Vinyl Furans/Thiophenes: Oxidative Heck Coupling under High-Speed Ball-Milling Conditions

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