Copper(I) Bromide-Catalyzed for the Synthesis of Sulfoxonium Ylides

doi:10.6023/cjoc201504005

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (9): 1961-1965.DOI: 10.6023/cjoc201504005 Previous Articles Next Articles

Articles

溴化亚铜催化合成二甲亚砜叶立德的新方法

张宏宇, 黄靖, 杨尚东

兰州大学功能有机分子国家重点实验室兰州 730000

收稿日期:2015-04-07 修回日期:2015-05-04 发布日期:2015-05-08
通讯作者: 杨尚东 E-mail:yangshd@lzu.edu.cn
基金资助:
国家自然科学基金(No. 21272100)资助项目.

Copper(I) Bromide-Catalyzed for the Synthesis of Sulfoxonium Ylides

Zhang Hongyu, Huang Jing, Yang Shangdong

State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000

Received:2015-04-07 Revised:2015-05-04 Published:2015-05-08
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21272100).

1. Copper(I) Bromide-Catalyzed for the Synthesis of Sulfoxonium Ylides.PDF(2389KB)

Cite this article

Zhang Hongyu, Huang Jing, Yang Shangdong. Copper(I) Bromide-Catalyzed for the Synthesis of Sulfoxonium Ylides[J]. Chin. J. Org. Chem., 2015, 35(9): 1961-1965.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

[1] (a) Padwa, A.; Hornbuckle, S. H. Chem. Rev. 1991, 91, 263. (b) Wang, Q.-G.; Deng, X.-M.; Zhu, B.-H.; Ye, L.-W.; Sun, X.-L.; Li, C.-Y.; Zhu, C.-Y.; Shen, Q.; Tang, Y. J. Am. Chem. Soc. 2008, 130, 5408.(c) Li, Y.; Huang, Z.; Xu, P.-F.; Zhang, Y.; Wang, J. Acta Chim. Sinica 2012, 70, 2024 (in Chinese). (李玉叶, 黄重行, 许鹏飞, 张艳, 王剑波, 化学学报, 2012, 70, 2024.)(d) Li, G.; Wang, L.; Huang, Y. Chin. J. Org. Chem. 2013, 33, 1900 (in Chinese). (李公春, 王利叶, 黄有, 有机化学, 2013, 33, 1900.)(e) Ma, M.; Peng, L.; Zhang, X.; Wang, J. Chin. J. Org. Chem. 2005, 25, 408 (in Chinese).(马明, 彭玲玲, 张秀, 王剑波, 有机化学, 2005, 25, 408.) (f) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730.(g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1997, 1231. (h) Qu, J.-P.; Xu, Z.-H.; Zhou, J.; Cao, C.-L.; Sun, X.-L.; Dai, L.-X.; Tang, Y. Adv. Synth. Catal. 2009, 351, 308. (i) Ma, M.; Peng, L.; Li, C.; Zhang, X.; Wang, J. J. Am. Chem. Soc. 2005, 127, 15016.(j) Lu, L.-Q.; Zhang, J.-J.; Li, F.; Cheng, Y.; An, J.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2010, 49, 4495.(k) Yang, Q.-Q.; Xiao, C.; Lu, L.; An, J.; Tan, F.; Li, B.-J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 9137.(l) Lu, L.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278. (m) Chen, Z.; Zhang, J. Chem. Asian J. 2009, 4, 1527.(n) Jiang, Y.; Ma, D. Tetrahedron: Asymmetry 2002, 13, 1033.
[2] (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867.(b) Corey, E. J.; Chaykovsky, M. J.Am. Chem. Soc. 1964, 86, 1640.(c) Corey, E. J.; Chaykovsky, M. Tetrahedron Lett. 1963, 4, 169. (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.(e) Gololobov, Y.G.; Nesmeyanov, A. N.; Lysenko, V. P.; Boldeskul, I. E. Tetrahedron 1987, 43, 2609. (f) Bernard, A.M.; Frongia, A.; Piras, P.P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565.(g) Kakei, H.; Sone, T.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 13410.(h) Yamashita, M.; Okuyama, K.; Kawajiri, T.; Ohta, S. Tetrahedron 2002, 58, 1497
[3] (a) Schomaker, J. M.; Bhattacharjee, S.; Yan, J.; Borhan, B. J. Am. Chem. Soc. 2007, 129, 1996. (b) Hodgson, D. M.; Fleming, M. J.; Xu, Z. Q.; Stanway, S. J. Chem. Commun. 2006, 3226. (c) Molinaro, C.; Bulger, P. G.; Lee, E. E.; Kosjek, B.; Lau, S.; Gauvreau, D.; Howard, M. E.; Wallace, D. J.; O'Shea, P. D. J. Org. Chem. 2012, 77, 2299(d) Luong, H.; Luss-Lusis, E.; Tanoury, G. J.; Nugent, W. A. Eur. J. Org. Chem. 2013, 4238.(e) Mangion, I. K.; Nwamba, I. K.; Shevlin, M.; Huffman, M. A. Org. Lett. 2009, 11, 3566.
[4] Guan, X.-Y.; Liu, Z.-Q.; Huang, H.-X.; Yang, L.-P.; Jian, L.; Hu, W.-H. Synlett 2009, 2183.
[5] (a) Gao, B.-L.; Ma, S.-T.; Liu, Z.-P. Lett. Org. Chem. 2009, 6, 648.(b) Tamura, Y.; Taniguchi, H.; Miyamoto, T.; Tsunekawa, M.; Ikeda, M. J.Org. Chem. 1974, 39, 3519.(c) Wang, D.; Schwinden, M. D.; Radesca, L.; Patel, B.; Kronenthal, D.; Huang, M.-H.; Nugent, W. A. J. Org. Chem. 2004, 69, 1629.
[6] (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.(b) Xiao, Q.; Wang, J.-B. Acta Chim. Sinica 2007, 65, 1733 (in Chinese). (肖卿, 王剑波, 化学学报, 2007, 65, 1733.)(c) Zhu, Y.; Liu, X.; Dong, S.; Zhou, Y.; Li, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2014, 53, 1636.(d) Ren, L.; Lian, X.-L.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 3315.(e) Qiu, L.; Guo, X.; Ma, C.; Qiu, H.; Liu, S.; Yang, L. P.; Hu, W. Chem. Commun. 2014, 50, 2196.(f) Qiu, L.; Gao, L.; Tang, J.; Wang, D.; Guo, X.; Liu, S.; Yang, L.; Li, J.; Hu, W. J. Org. Chem. 2014, 79, 4142.(g) Liu, C.-R.; Zhu, B.-H.; Zheng, J.-C.; Sun, X.-L.; Xie, Z.; Tang, Y. Chem. Commun. 2011, 47, 1342.(h) Liu, B.; Zhu, S.-F.; Zhang, W.; Chen, C.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 5834.
[7] (a) Furukawa, N.; Takahashi, F.; Yoshimura, T.; Oae, S. Tetrahedron Lett. 1977, 18, 3633.(b) Furukawa, N.; Takahashi, F.; Yoshimura, T.; Oae, S. Tetrahedron 1979, 35, 317.
[8] (a) Dost, F.; Gosselck, J. Chem. Ber. 1972, 105, 948. (b) Dost, F.; Gosselck, J. Tetrahedron Lett. 1970, 11, 5091.
[9] (a) Pang, W.; Zhu, S.; Xing, C.; Luo, N.; Jiang, H.; Zhu, S. J. Fluorine Chem. 2008, 129, 343.(b) Moody, C. J.; Taylor, R. J. Tetrahedron Lett. 1988, 29, 6005. (c) Moody, C. J.; Slawin, A. M. Z.; Taylor, R. J.; Williams, D. J. Tetrahedron Lett. 1988, 29, 6009.(d) Moody, C. J.; Taylor, R. J. Tetrahedron 1990, 46, 6525.(e) Suarez, A. I. O.; del Río, M. P.; Remerie, K.; Reek, J. N. H.; de Bruin, B. ACS Catal. 2012, 2, 2046.
[10] (a) Zhu, S.; Zhu, S.; Liao, Y. J. Fluorine Chem. 2004, 125, 1071.(b) Takebayashi, M.; Kashiwada, T.; Hamaguchi, M.; Ibata, T. Chem. Lett. 1973, 809.(c) Ando, W.; Yagihara, T.; Tozune, S.; Imai, I.; Suzuki, J.; Toyama, T.; Nakaido, S.; Migita, T. J. Org. Chem. 1972, 37, 1721.(d) Ando, W.; Yagihara, T.; Tozune, S.; Nakaido, S.; Migita, T. Tetrahedron Lett. 1969, 10, 1979.

[1]	Yu Tian, Juan Zhang, Wenchao Gao, Honghong Chang. Application of Dimethyl Sulfoxide as Methylating Reagent in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2391-2406.
[2]	Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498.
[3]	Zhen Tang, Chao Pi, Yangjie Wu, Xiuling Cui. Rhodium-Catalyzed Tandem Acylmethylation/Annulation Reactions of 2-Aryl-2H-indazoles with Sulfoxonium Ylides: Easy Access to 6-Arylindazolo[2,3-a]quinolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1187-1196.
[4]	Jiantao Zhang, Cong Zhang, Zidong Zheng, Peng Zhou, Weibing Liu. Research Progress of Sulfoxonium Ylides in the Construction of Five/Six-Membered Nitrogen-Containing Heterocycles [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2745-2759.
[5]	Yuliang Qian, Lan Xu, Yihan Tong, Tianyi Liu, Yingying Xia, Dingmao Hu, Liangce Rong. Synthesis of 2-Substituted Cyclopenta[c]chromene Derivatives by α-C Insertion of Acetonitrile (Acetone) [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 181-189.
[6]	Sai Shu, Zhibin Huang, Yujie Chen, Shan Yang, Yaqiqi Jiang, jingyu Zhang, Yingsheng Zhao. Rh(III)-Catalyzed [4+2] Annulation of Indoles with Sulfoxonium Ylides for the Synthesis of Dihydropyrimidoindolone Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3171-3179.
[7]	Cong Wang, Yaoyao Yao, Jun Xie, Jianta Wang, Feiqing Wang, Jiquan Zhang, Lei Tang. Convenient Method for Preparingα-Ketoarylthioamide by Air Oxidation under Base Conditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 370-375.
[8]	Liu Yufeng, Cao Zhongzhong, Su Miaodong, Li Hui, Fu Meiqiang, Liu Qiang, Luo Weiping, Guo Cancheng. Iron(Ⅲ) Porphyrin Catalyzed Cyclization of Ketones with Dimethyl Sulfoxide and Ammonium Acetate: One-Pot Synthesis of Pyridines [J]. Chin. J. Org. Chem., 2019, 39(1): 129-136.
[9]	Meng Tuanjie, Feng Cuilan, Liu Lantao, Wang Tao, Xu Kai, Zhao Wenxian. Palladium Catalyzed Oxidation of Ynamides Using Dimethyl Sulfoxide as Oxidant: A Facile Way to Synthesize α-Ketoamide Derivatives [J]. Chin. J. Org. Chem., 2016, 36(6): 1382-1388.
[10]	Xu Xing, Guan Yaohui, Xu Dongcheng, Li Xinsheng. Copper(I)-Catalyzed Oxidation of Disubstituted Aromatic Alkenes to Ketones [J]. Chin. J. Org. Chem., 2016, 36(4): 850-854.
[11]	Xu Xing, Xu Dongcheng, Li Xinsheng. 1,2-Di-tert-butyldiaziridinone-Cu Catalyzed Oxidation of Alkenes to Ketones [J]. Chin. J. Org. Chem., 2016, 36(10): 2479-2483.
[12]	Wang Kou, Yu Haofei, Ding Linfen, Hu Jianlin. CuBr₂-Catalyzed Three-Component Coupling for Synthesis of Quinoline-2,4-dicarboxyl Derivatives [J]. Chin. J. Org. Chem., 2014, 34(7): 1437-1441.
[13]	Chen Pingliang, Lu Shijie, Hu Xingen, Xu Qing. CsOH/DMSO Promoted Reactions of Aryl Halides with Phenols: A Convenient Method for the Synthesis of Diaryl Ethers [J]. Chin. J. Org. Chem., 2014, 34(1): 112-117.
[14]	ZHOU Lei,b,c, JIANG Huan-Feng*^,c. A Stereocontrolled Route to Conjugated E-Enediynes [J]. Chin. J. Org. Chem., 2006, 26(12): 1682-1695.
[15]	ZUO, Hua, ZHAO, Bao-Xiang, TAN, Wei, WANG, Da-Wei, SHA, Lei. Synthesis of 1,3-Dihydroxyacetone Derivatives [J]. Chinese Journal of Organic Chemistry, 2004, 24(3): 331-333.

溴化亚铜催化合成二甲亚砜叶立德的新方法

Copper(I) Bromide-Catalyzed for the Synthesis of Sulfoxonium Ylides

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments