空气条件下亚甲基桥连1,3-二羰基化合物的合成
收稿日期: 2014-12-20
修回日期: 2015-02-02
网络出版日期: 2015-02-10
基金资助
国家重点基础研究发展计划(973计划, No. 2012CBA01204)和国家自然科学基金(No. 21302084)资助项目.
Synthesis of Methylene-Bridged Bis-1,3-dicarbonyl Compounds under Aerobic Condition
Received date: 2014-12-20
Revised date: 2015-02-02
Online published: 2015-02-10
Supported by
Project supported by the National Key Basic Research Program of MOST of China (973 Program, No. 2012CBA01204) and the National Natural Science Foundation of China (No. 21302084).
郭生梅 , 龚久涵 , 卢林 , 朱正 , 蔡琥 . 空气条件下亚甲基桥连1,3-二羰基化合物的合成[J]. 有机化学, 2015 , 35(6) : 1348 -1352 . DOI: 10.6023/cjoc201412035
A simple route for the preparation of methylene-bridged bis-1,3-dicarbonyl compounds was achived through a cleavage of C—N bond of tertiary amines. In this reaction, tetramethylethylenediamine (TMEDA) was used as the methylene source, and cuprous iodide as catalyst under aerobic condition. The substrates bearing different substituents were tolerated well and afforded the corresponding products with moderate to good yields.
Key words: air; tertiary amines; C—N bond cleavage; methylene-bridged compounds
[1] (a) Shono, T.; Nishiguchi, I.; Komamura, T.; Sasaki, M. J. Am. Chem. Soc 1979, 101, 984. (b) Kupchan, S. M.; Eakin, M. A.; Thomas, A. M. J. Med. Chem. 1971, 14, 1147. (c) Lee, K.-H.; Huang, E.-S.; Piantadosi, C.; Pagano, J. S.; Geissmann, T. A. Cancer Res. 1971, 31, 1649.
[2] (a) Huet, F.; Pellet, M.; Conia, J. M. Tetrahedron Lett. 1977, 18, 3505. (b) Holy, N. L.; Wang, Y. F. J. Am. Chem. Soc. 1977, 99, 944. (c) Ksander, G. M.; McMurry, J. E.; Johnson, M. J. Org. Chem. 1977, 42, 1180. (d) Grieco, P. A. Syntheis 1975, 67.
[3] (a) Hedge, J. A.; Kruse, C. W.; Snyder, H. R. J. Org. Chem. 1961, 26, 3166. (b) Abdallah-E Ayoubi, S.; Texier-Boullet, F.; Hamelin, J. Synthesis 1994, 258. (c) Maruyama, K.; Kubo, K.; Toda, Y.; Kawase, K.; Mashino, T.; Nishinaga, A. Tetrahedron. Lett. 1995, 36, 5609. (d) Kaupp, G.; Naimi-Jamal, M. R.; Schmeyers, J. Tetrahedron 2003, 59, 3753. (e) Blakemore, P. R.; Kilner, C.; Norcross, N. R.; Astles, P. C. Org. Lett. 2005, 7, 4721. (f) Breuning, M.; Steiner, M.; Mehler, C.; Paasche, A. Hein, D. J. Org. Chem. 2009, 74, 1407. (g) Tahmassebia, D.; Wilsona, L. J. A.; Kiesera, J. M. Synth. Commun. 2009, 39, 2605. (h) Gu, Y.; Sousa, R.; Frapper, G.; Barrault, J. Green Chem. 2009, 11, 1968. (i) Gu, Y.; Barrault, J.; Jérôme, F. Adv. Synth. Catal. 2009, 351, 3269. (j) Tan, J.; Li, H.; Gu, Y. Green Chem. 2010, 12, 1772.
[4] (a) Newkome, G. R.; Baker, G. R.; Arai, S.; Saunders, M.; Russo, P. S.; Theriot, K. J.; Moorefield, C. N.; Edward Rogers, L.; Miller, J. E. J. Am. Chem. Soc. 1990, 112, 8458. (b) Hon, Y.-S.; Hsu, T.-R.; Chen, C.-Y.; Lin, Y.-H.; Chang, F.-J.; Hsieh, C.-H.; Szu, P.-H. Tetrahedron 2003, 59, 1509. (c) Lecomte, V.; Bolm, C. Adv. Synth. Catal. 2005, 347, 1666. (d) Hwang, D.-R.; Uang, B.-J. Org. Lett. 2002, 4, 463.
[5] (a) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215. (b) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068. (c) Wendlandt, A. E.; Suess, A. M.; Stahl, S. S. Angew. Chem., Int. Ed. 2011, 50, 11062. (d) Shi, Z.; Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3381. (e) Campbell, A. N.; Stahl, S. S. Acc. Chem. Res. 2012, 45, 851. (f) Li, C.-J. Acc. Chem. Res. 2009, 43, 335. (g) Li, Y.; Ma, L.; Li, Z. Chin. J. Org. Chem. 2013, 33, 704 (in Chinese). (李远明, 马丽娜, 李志平, 有机化学, 2013, 33, 704.) (h) Guo, X.; Li, Z.; Li, C. Prog. Chem. 2010, 22, 1434 (in Chinese). (郭兴伟, 李志平, 李朝军, 化学进展, 2010, 22, 1434.)
[6] (a) Li, H.; He, Z.; Guo, X.; Li, W.; Zhao, X.; Li, Z. Org. Lett. 2009, 11, 4176. (b) Liu, W.; Liu, J.; Ogawa, D.; Nishihara, Y.; Guo, X.; Li, Z. Org. Lett. 2011, 13, 6272.
[7] Balamurugan, R.; Manojveer, S. Chem. Commun. 2011, 47, 11143.
[8] Yoo, W.-J.; Tanoue, A.; Kobayashi, S. Chem. Asian J. 2012, 7, 2764.
[9] Xu, X.; Ge, Z.; Cheng, D.; Li, X. ARKIVOC 2012, (viii), 107
[10] Lu, L.; Guo, S.; Xiong, Q.; Liu, S.; Li, X.; Cai, H. Synthesis 2014, 46, 2445.
[11] (a) Zhao, D.; Wang, Y.; Zhu, M.-X.; Shen, Q.; Zhang, L.; Du, Y.; Li, J.-X. RSC Adv. 2013, 3, 10272. (b) Wang, X.; Wang, Y.; Yuan, Y.; Xing, C.-H.; Tetrahedron 2014, 70, 2195.
[12] (a) Chen, J.; Liu, B.; Liu, D,; Liu, S.; Cheng, J. Adv. Synth. Catal. 2012, 354, 2438. (b) Zhang, L.; Peng, C.; Zhao, D.; Wang, Y.; Fu, H.-J.; Shen, Q.; Li, J.-X. Chem. Commun. 2012, 48, 5928.
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