SIOC English
有机化学
高级检索

有机化学 >

2015 , Vol. 35 >Issue 9: 1820 - 1833

DOI: https://doi.org/10.6023/cjoc201503007

综述与进展

过渡金属催化非活化烷基卤化物C(sp3)—C(sp3)交叉偶联反应研究进展

  • 张文曼 ,
  • 戴建军 ,
  • 许华建
展开
  • 合肥工业大学医学工程学院 合肥 230009

收稿日期: 2015-03-04

  修回日期: 2015-05-28

  网络出版日期: 2015-06-04

基金资助

国家自然科学基金(Nos. 21472033, 21402036, 21272050)、中国博士后科学基金(No. 2014M551793)和中央高校基本科研业务费专项资金(No. 2013HGBH0046)资助项目.

收起

Recent Advances of Transition Metal-Catalyzed C(sp3)—C(sp3) Cross-Coupling Reactions of Non-activated Alkyl Halides

  • Zhang Wenman ,
  • Dai Jianjun ,
  • Xu Huajian
Expand
  • School of Medical Engineering, Hefei University of Technology, Hefei 230009

Received date: 2015-03-04

  Revised date: 2015-05-28

  Online published: 2015-06-04

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21472033, 21402036, 21272050), the China Postdoctoral Science Foundation (No. 2014M551793), and the Fundamental Research Funds for the Central Universities (No. 2013HGBH0046).

Fold

摘要

近年来, 过渡金属催化非活化烷基卤化物应用于构建C(sp3)—C(sp3)化学键受到广泛关注. 由于非活化烷基卤化物和金属催化剂发生氧化加成困难, 得到的氧化加成中间体容易发生β-H消除等因素使非活化烷基卤化物和烷基亲核试剂的交叉偶联成为一项挑战. 综述了过渡金属催化非活化烷基卤化物C(sp3)—C(sp3)交叉偶联反应的新进展, 探讨了不同催化体系下反应的机理及应用范围.

关键词： 过渡金属; 催化; 非活化烷基卤化物; 交叉偶联; 进展

本文引用格式

张文曼 , 戴建军 , 许华建 . 过渡金属催化非活化烷基卤化物C(sp3)—C(sp3)交叉偶联反应研究进展[J]. 有机化学, 2015 , 35(9) : 1820 -1833 . DOI: 10.6023/cjoc201503007

Abstract

Recently, great attention has been directed to the transition-metal-catalyzed cross-coupling reactions of non-acti-vated alkyl halides for the construction of C(sp3)—C(sp3) bonds. However, due to the difficulty of oxidative addition of the non-activated alkyl halides with a metal catalyst and the resulting metal-alkyl intermediate prone to β-H elimination, the cross-coupling of non-activated alkyl halides with alkyl nucleophiles remains a challenge. This review summarizes the recent advances of C(sp3)—C(sp3) cross-coupling of non-activated alkyl halides catalyzed by transition-metals.

Key words： transition-metal; catalyze; non-activated alkyl halide; cross-coupling; advance

参考文献

[1] (a) Frisch, A. C.; Beller, M. Angew. Chem., Int. Ed. 2005, 44, 674. (b) Netherton, M. R.; Fu, G. C. Topics in Organometallic Chemistry: Palladium in Organic Synthesis, Ed.: Tsuji, J., Springer, New York, 2005. (c) Netherton, M. R.; Fu, G. C. Adv. Synth. Catal. 2004, 346, 1525. (d) Liu, Y.-L.; Zhang, Y.-H.; Fei, H.-Y.; Jin, X.-H. Chin. J. Org. Chem. 2013, 33, 267 (in Chinese). (刘雅莉, 张韻慧, 费红艳, 晋兴华, 有机化学, 2013, 33, 267.)(e) Liu, Z.-X.; Zhang, Y.; Wang, J.-B. Chin. J. Org. Chem. 2013, 33, 687 (in Chinese). (刘振兴, 张艳, 王剑波, 有机化学, 2013, 33, 687.)(f) Yang, J.; Deng, M.-Z.; Yu, T. Chin. J. Org. Chem. 2013, 33, 693 (in Chinese). (杨军, 邓敏智, 于涛, 有机化学, 2013, 33, 693.)(g) Zhang, Y.; Feng, B.-N. Chin. J. Org. Chem. 2014, 34, 2406 (in Chinese). (张艳, 冯柏年, 有机化学, 2014, 34, 2406.)(h) Wang, B.-Y.; Ni, P.-Z.; Fan, J.-L.; Zheng, H.-D; Zhao, S.-Y.; Bai, Z.-S. Chin. J. Org. Chem. 2014, 34, 2471 (in Chinese). (王碧玉, 倪沛钟, 范吉理, 郑辉东, 赵素英, 白正帅, 有机化学, 2014, 34, 2471.)
[2] (a) Keaton, K. A.; Phillips, A. J. Org. Lett. 2007, 9, 2717. (b) Geist, E.; Kirschning, A.; Schmidt, T. Nat. Prod. Rep. 2014, 31, 441.
[3] Schmidt, T.; Kirschning, A. Angew. Chem., Int. Ed. 2012, 51, 1063.
[4] Li, Z.; Liu, L. Chin. J. Catal. 2015, 36, 3.
[5] Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2007, 129, 9602.
[6] Saito, B.; Fu, G. C. J. Am. Chem. Soc. 2008, 130, 6694.
[7] Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2010, 132, 11908.
[8] Lu, Z.; Fu, G. C. Angew. Chem., Int. Ed. 2010, 49, 6676.
[9] Lu, Z.; Wilsily, A.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 8154.
[10] Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu. G. C. J. Am. Chem. Soc. 2012, 134, 5794.
[11] Cordier, C. J.; Lundgren, R. J.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 10946.
[12] Jiang, X.; Sakthivel, S.; Kulbitski, K.; Nisnevich, G.; Gandelman, M. J. Am. Chem. Soc. 2014, 136, 9548.
[13] (a) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 14726. (b) Yi, J.; Lu, X.; Sun, Y.-Y.; Xiao, B.; Liu, L. Angew. Chem., Int. Ed. 2013, 52, 12409.
[14] Anderson, T. J.; Jones, G. D.; Vicic, D. A. J. Am. Chem. Soc. 2004, 126, 8100.
[15] Jones, G. D.; McFarland, C.; Anderson, T. J.; Vicic, D. A. Chem. Commun. 2005, 4211.
[16] Csok, Z.; Vechorkin, O.; Harkins, S. B.; Scopelliti, R.; Hu, X. J. Am. Chem. Soc. 2008, 130, 8156.
[17] Vechorkin, O.; Hu, X. Angew. Chem., Int. Ed. 2009, 48, 2937.
[18] Garcia, P. M. P.; Franco, T. D.; Orsino, A.; Ren, P.; Hu, X. Org. Lett. 2012, 14, 4286.
[19] Yu, X.; Yang, T.; Wang, S.; Xu, H.; Gong, H. Org. Lett. 2011, 13, 2138.
[20] Liang, Z.; Xue, W.; Lin, K.; Gong, H. Org. Lett. 2014, 16, 5620.
[21] Lu, X.; Yi, J.; Zhang, Z.-Q.; Dai, J.-J.; Liu, J.-H.; Xiao, B.; Fu, Y.; Liu, L. Chem. Eur. J. 2014, 20, 15339.
[22] Giovannini, R.; Stüdemann, T.; Dussin, G.; Knochel, P. Angew. Chem., Int. Ed. 1998, 37, 2387.
[23] Terao, J.; Watanabe, H.; Ikumi, A.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2002, 124, 4222.
[24] Terao, J.; Todo, H.; Watanabe, H.; Ikumi, A.; Kambe, N. Angew. Chem., Int. Ed. 2004, 43, 6180.
[25] Wu, X.; Zhao, Y.; Ge, H. J. Am. Chem. Soc. 2014, 136, 1789.
[26] Ishiyama, T.; Abe, S.; Miyaura, N.; Suzuki, A. Chem. Lett. 1992, 691.
[27] (a) Netherton, M. R.; Dai, C.; Neuschütz, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 10099. (b) Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945. (c) Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 3910.
[28] Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 13662.
[29] Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527.
[30] Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Org. Lett. 2005, 7, 3805.
[31] Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. J. Org. Chem. 2005, 70, 8503.
[32] O’Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem.-Eur. J. 2006, 12, 4743.
[33] Peh, G.-R.; Kantchev, E. A. B.; Er, J.-C.; Ying, J. Y. Chem.-Eur. J. 2010, 16, 4010.
[34] Achonduh, G. T.; Hadei, N.; Valente, C.; Avola, S.; O’Brien, C. J.; Organ, M. G. Chem. Commun. 2010, 46, 4109.
[35] McCann, L. C.; Hunter, H. N.; Clyburne, J. A. C.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 7024.
[36] Terao, J.; Naito, Y.; Kuniyasu, H.; Kambe, N. Chem. Lett. 2003, 32, 890.
[37] Chen, X.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 12634.
[38] Wang, D.-H.; Wasa, M.; Giri, R.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 7190.
[39] Zhu, R.-Y.; He, J.; Wang, X.-C.; Yu, J.-Q. J. Am. Chem. Soc. 2014, 136, 13194.
[40] Shabashov D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
[41] Zhang, S.-Y.; He, G.; Nack, W. A.; Zhao, Y.; Li, Q.; Chen, G. J. Am. Chem. Soc. 2013, 135, 2124.
[42] Zhang, S.-Y.; Li, Q.; He, G.; Nack, W. A.; Chen, G. J. Am. Chem. Soc. 2013, 135, 12135.
[43] Chen, K.; Hu, F.; Zhang, S.-Q.; Shi, B.-F. Chem. Sci. 2013, 4, 3906.
[44] Chen, K.; Shi, B.-F. Angew. Chem., Int. Ed. 2014, 53, 11950.
[45] Cahiez, G.; Chaboche, C.; Jézéquel, M. Tetrahedron 2000, 56, 2733.
[46] Yang, C.-T.; Zhang, Z.-Q.; Liu, Y.-C.; Liu, L. Angew. Chem., Int. Ed. 2011, 50, 3904.
[47] Yang, C.-T.; Zhang, Z.-Q.; Tajuddin, H.; Wu, C.-C.; Liang, J.; Liu, J.-H.; Fu, Y.; Czyzewska, M.; Steel, P. G.; Marder, T. B.; Liu, L. Angew. Chem., Int. Ed. 2012, 51, 528.
[48] Ren, P.; Stern L.-A.; Hu, X. Angew. Chem., Int. Ed. 2012, 51, 9110.
[49] Zhang, Z.-Q.; Yang, C.-T.; Liang, L.-J.; Xiao, B.; Lu, X.; Liu, J.-H.; Sun, Y.-Y.; Marder, T. B.; Fu, Y. Org. Lett. 2014, 16, 6342.
[50] Donkervoort, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H. R.; Gossage, A.; Cahiez, G.; van Koten, G. J. Organomet. Chem. 1998, 558, 61.
[51] Yang, C.-T.; Zhang, Z.-Q.; Liang, J.; Liu, J.-H.; Lu, X.-Y.; Chen, H.-H.; Liu, L. J. Am. Chem. Soc. 2012, 134, 11124.
[52] Terao, J.; Todo, H.; Begum, S. A.; Kuniyasu, H.; Kambe, N. Angew. Chem., Int. Ed. 2007, 46, 2086.
[53] Shen, R.; Iwasaki, T.; Terao, J.; Kambe, N. Chem. Commun. 2012, 48, 9313.
[54] Kim, J. H.; Chung, Y. K. Chem. Commun. 2013, 49, 11101.
[55] Iwasaki, T.; Imanishi, R.; Shimizu, R.; Kuniyasu, H.; Terao, J.; Kambe, N. J. Org. Chem. 2014, 79, 8522.
[56] Liu, J.-H.; Yang, C.-T.; Lu, X.-Y.; Zhang, Z.-Q.; Xu, L.; Cui, M.; Lu, X.; Xiao, B.; Fu, Y.; Liu, L. Chem.-Eur. J. 2014, 20, 15334.
[57] Someya, H.; Yorimitsu, H.; Oshima. K. Tetrahedron Lett. 2009, 50, 3270.
[58] Zhou, W.; Napoline, J. W.; Thomas, C. M. Eur. J. Inorg. Chem. 2011, 2029.
[59] Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura M. Angew. Chem., Int. Ed. 2012, 51, 8834.
[60] Iwasaki, T.; Takagawa, H.; Singh, S. P.; Kuniyasu, H.; Kambe, N. J. Am. Chem. Soc. 2013, 135, 9604.
[61] Guisan-Ceinos, M.; Tato, F.; Bunuel, E.; Calle, P.; Cardenas, D. J. Chem. Sci. 2013, 4, 1098.

Options
文章导航

/

〈 〉