α,α'-双亚甲基锆杂环戊烷的构建及其在1,5-己二烯合成中的应用
收稿日期: 2014-12-31
修回日期: 2015-01-25
网络出版日期: 2015-01-28
基金资助
国家自然科学基金(No. 20972037)、浙江省重点科技创新团队建设项目(No. 2010R50017)、杭州师范大学优秀中青年教师支持计划(No. HNUEYT-2011-01-013)、教育部创新团队长江学者和创新团队发展计划(No. IRT1231)资助项目.
Preparation of α,α'-Bismethylenyl Zirconacyclopentane and Its Application in the Synthesis of 1,5-Hexadiene Derivatives
Received date: 2014-12-31
Revised date: 2015-01-25
Online published: 2015-01-28
Supported by
Project supported by the National Natural Science Foundation of China (No. 20972037), the Special Funds for Key Innovation Team of Zhejiang Province (No. 2010R50017), the Excellent Young Teacher Support Program of Hangzhou Normal University (No. HNUEYT-2011-01-013) and the Program for Changjiang Scholars and Innovative Research Team in Chinese University (No. IRT1231).
锆杂环化合物因其多种反应活性而备受关注. 2分子1,1-二取代联烯在低价锆物种"Cp2Zr(II)"作用下可发生分子间还原偶联形成α,α'-双亚甲基锆杂环戊烷, 反应的区域及立体化学受到取代基空间效应影响显著. α,α'-双亚甲基锆杂环戊烷中含有两个sp2碳-金属键, 与多种亲电试剂体系反应分别生成多种类型有机分子, 可为2,5-二卤代-1,5-己二烯、具有1,5-二烯骨架的1,6-二羰基化合物等多功能有机分子提供新合成方法学.
关键词： α,α'-双亚甲基锆杂环戊烷; 1,5-己二烯; 合成; 选择性
胡麟峰 , 王伟 , 章彦婧 , 林胜 , 陆红燕 , 郑卫新 . α,α'-双亚甲基锆杂环戊烷的构建及其在1,5-己二烯合成中的应用[J]. 有机化学, 2015 , 35(3) : 662 -671 . DOI: 10.6023/cjoc201412058
Zirconacycle has attached much attention owing to its various reactive behaviors. α,α'-Bismethylenyl zirconacyclopentane could be prepared by reductive coupling reaction of two 1,1-disubstituted allenes promoted by low covalent zirconocene species "Cp2Zr (II)". The stereo- and regio-chemistry could be affected obviously by steric and electronic effect of the substituents in the allenes. Two sp2 carbon-metallic bonds in α,α'-bismethylenyl zirconacyclopentane could be quenched by several electrophilic system and afford the novel methodologies for the synthesis of 1,1,6,6-tetrasubstituted 1,5-hexadiene, 2,5-dihalo-1,5-hexadiene and 1,6-dicarbonyl compound with the skeleton of 1,5-hexadiene.
[1] (a) Xi, Z. Top. Catal. 2005, 35, 63. (b) Xi, Z.; Li, Z. Top. Organomet. Chem. 2004, 8, 27. (c) Jemmis, E. D.; Roy, S.; Burlakov, V. V.; Jiao, H.; Klahn, M.; Hansen, S.; Rosenthal, U. Organometallics 2010, 29, 76. (d) Liu, J. H.; Zhang, W. X.; Guo, X. Y.; Hou, Z. M.; Xi, Z. F. Organometallics 2007, 26, 6812. (e) Zhou, L.; Yamanaka, M.; Kanno, K.; Takahashi, T. Heterocycles 2008, 76, 923. (f) Chen, C.; Xi, C. Chin. Sci. Bull. 2010, 55, 3235. (g) Mao, K.; Fu, X.; Liu, D.; Li, S.; Liu, Y. Chin. J. Org. Chem. 2013, 33, 780 (in Chinese). (毛可彬, 付晓平, 刘丹, 李石, 刘元红, 有机化学, 2013, 33, 780.) (h) Zhao, J.; Zhang, S.; Zhang, W.; Xi, Z. Organometallics 2011, 30, 3464. (i) Zhang, S.; Zhao, J.; Zhang, W.; Xi, Z. Org. Lett. 2011, 13, 1626. (j) Zhang, S.; Zhang, W.; Xi, Z. Chem. Eur. J. 2010, 16, 8419. (k) Wang, C.; Deng, L.; Yan, J.; Wang, H.; Luo, Q.; Zhang, W.; Xi, Z. Chem. Commun. 2009, 4414. (l) Xi, Z.; Zhang, W. Synlett 2008, 2557.
[2] (a) Geng, W. Z.; Wang, C.; Guang, J.; Hao, W.; Zhang, W. X.; Xi, Z. F. Chem. Eur. J. 2013, 19, 8657. (b) Wang, C.; Xi, Z. Chem. Soc. Rev. 2007, 36, 1395. (c) Hu, Q.; Lu, J.; Wang, C.; Wang, C.; Xi, Z. Tetrahedron 2007, 63, 6614. (d) Lu, J.; Mao, G.; Zhang, W.; Xi, Z. Chem. Commun. 2005, 4848. (e) Xi, Z.; Fan, H.-T.; Mito, S.; Takahashi, T. J. Organomet. Chem. 2003, 682, 108. (f) Zhao, C.; Yan, J.; Xi, Z. J. Org. Chem. 2003, 68, 4355. (g) Zhao, C.; Li, P.; Cao, X.; Xi, Z. Chem. Eur. J. 2002, 8, 4292. (h) Xi, Z.; Li, P. Angew. Chem., Int. Ed. 2000, 39, 2950.
[3] (a) Zhang, W. X.; Zhang, S. G.; Xi, Z. F. Acc. Chem. Res. 2011, 44, 541. (b) Zhang, S. G.; Zhang, W. X.; Zhao, J.; Xi, Z. F. J. Am. Chem. Soc. 2010, 132, 14042. (c) Zhang, W. X.; Zhang, S. G.; Sun, X. H.; Nishiura, M.; Hou, Z. M.; Xi, Z. F. Angew. Chem., Int. Ed. 2009, 48, 7227. (d) Zhao, J.; Zhang, S.; Zhang, W.-X.; Xi, Z. Coord. Chem. Rev. 2014, 270～271, 2. (e) Zhao, J.; Zhang, S.; Zhang, W.; Xi, Z. Organometallics 2012, 31, 8370.
[4] For benzene and polycyclic aromatic hydrocarbon, see: (a) Li, S.; Takahashi, T. In Transition-Metal-Mediated Aromatic Ring Construction, Vol. 11, Ed.: Tanaka, K., John Wiley& Sons, Inc., 2013, p. 299. (b) Ni, Y.; Nakajima, K.; Kanno, K.; Takahashi, T. Org. Lett. 2009, 11, 3702. (c) Seri, T.; Qu, H.; Zhou, L.; Kanno, K.; Takahashi, T. Chem. Asian J. 2008, 3, 388. For Indene, see: (d) Ren, S.; Igarashi, E.; Nakajima, K.; Kanno, K.; Tamotsu, T. J. Am. Chem. Soc. 2009, 131, 7492. For Co-oligomers of Thiophene Derivatives, see: (e) Payra, D.; Song, Z.; Kanno, K.; Takahashi, T. Chem. Lett. 2011, 40, 1447. For linear triene, see: (f) Kanno, K.; Igarashi, E.; Zhou, L.; Nakajima, K.; Takahashi, T. J. Am. Chem. Soc. 2008, 130, 5624.
[5] (a) Yu, S.; Sun, R.; Chen, H.; Xie, X.; Liu, Y. Chem. Eur. J. 2014, 20, 1. (b) Yu, S.; Xiong, M.; Xie, X.; Liu, Y. Angew. Chem., Int. Ed. 2014, 53, 11596.
[6] (a) Ren, S.; Chan, H. S.; Xie, Z. J. Am. Chem. Soc. 2009, 131, 3862. (b) Ren, S.; Chan, H. S.; Xie, Z. Organometallics 2009, 28, 4106.
[7] (a) Ma, S. Acc. Chem. Res. 2009, 42, 1679. (b) Cheng, X.; Jiang, X.; Yu, Y.; Ma, S. J. Org. Chem. 2008, 73, 8960. (c) Ma, S. Chem. Rev. 2005, 105, 2829. (d) Hassan, H. Curr. Org. Synth. 2007, 4, 413.
[8] (a) Bai, T.; Ma, S.; Jia, G. T. Coord. Chem. Rev. 2009, 253, 423. (b) Suzuki, N.; Hashizume, D.; Koshino, H.; Chihara, T. Angew. Chem., Int. Ed. 2008, 47, 5198 (c) Schmidt, J. R.; Duggan, D. M. Inorg. Chem. 1981, 20, 318; (d) Diversi, P.; Ingrosso, G.; Immirzi, A.; Zoccki, M. J. Organomet. Chem. 1976, 104, C1. (e) Binger, P.; Langhauser, F.; Wedemann, P.; Gabor, B.; Mynott, R.; Kruger, C. Chem. Ber. 1994, 127, 39. (f) Yin, J.; Abboud, K.; Jones, W. J. Am. Chem. Soc. 1993, 115, 8859. (g) Brummond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156. (h) Yin, J.; Jones, W. Tetrahedron 1995, 51, 4395.
[9] (a) Salvador, J. A. R.; Silvestre, S. M.; Pinto, R. M. A.; Santos, R. C.; LeRoux, C. Top. Curr. Chem. 2012, 311, 143. (b) Gershenzon, J.; Dudareva, N. Nat. Chem. Biol. 2007, 3, 408.
[10] (a) Lima, A. F.; Borges, G. R.; Candeco, L. M.; Pinto, J. C.; Nele, M.; Liberman, S. Polimeros 2012, 22, 253. (b) Shi, X. C.; Tang, X. Y.; Li, Y. S. Polymer 2011, 52, 3053. (c) Shi, X. C.; Wang, Y. X.; Liu, J. Y.; Cui, D. M.; Men, Y. F.; Li, Y. S. Macromolecules 2011, 44, 1062.
[11] (a) Harrison, J. G.; Tantillo, D. J. Phys. Chem. Chem. Phys. 2012, 14, 14756. (b) Graulich, N. Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2011, 1, 172. (c) Gul, S.; Schoenebeck, F.; Aviyente, V.; Houk, K. N. J. Org. Chem. 2010, 75, 2115. (d) Almendros, P.; Aragoncillo, C.; Cabrero, G.; Callejo, R.; Carrascosa, R.; Luna, A.; del Campo, T. M.; Pardo, M. C.; Quiros, M. T.; Redondo, M. C.; Rodriguez-Ranera, C.; Rodriguez-Vicente, A.; Ruiz, M. P. ARKIVOC 2010, 74.
[12] Zheng, W. X.; Wu, Y. F.; Zheng, F. F.; Hu, L. F.; Hong, Y. Tetrahedron Lett. 2010, 51, 4702.
[13] Takahashi, T.; Xi, Z.; Yamazaki, A.; Liu, Y.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672.
[14] (a) Wu, Y.; Zheng, W.; Zheng, F.; Yan, W. J. Hangzhou Normal Univ. (Nat. Sci. Ed.) 2010, 9, 124 (in Chinese). (吴阳锋, 郑卫新, 郑芬芬, 严微微, 杭州师范大学学报(自然科学版), 2010, 9, 124.) (b) Hu, L.; Zhang, Y.; Hong, Y.; Chen, C.; Mao, G.; Zheng, W. J. Hangzhou Normal Univ. (Nat. Sci. Ed.) 2012, 11, 346 (in Chinese). (胡麟峰, 章彦靖, 洪雅, 陈聪, 毛国梁, 郑卫新, 杭州师范大学学报(自然科学版), 2012, 11, 346.)
[15] Bertrand, M. P.; Surzur, J. M.; Oumar-Mahamat, H.; Moustrou, C. J. Org. Chem. 1991, 56, 3089.
/
| 〈 |
|
〉 |
