SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 7: 1638 - 1649

DOI: https://doi.org/10.6023/cjoc201802007

Reviews

Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C-C Bonds Activation Reactions

  • Wang Jingjing ,
  • Li Feng ,
  • Yu Xiaobo ,
  • Liu Lantao ,
  • Ding Junru ,
  • Xie Peiyao ,
  • Wang Jianhui
Expand
  • a Henan Engineering Laboratory of Green Synthesis for Pharmaceuticals, School of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000;
    b Department of Chemistry, College of Science, Tianjin University, Tianjin 300072;
    c College of Materials Science and Engineering, Jilin Institute of Chemical Technology, Jilin 132022

Received date: 2018-02-04

  Revised date: 2018-03-03

  Online published: 2018-03-16

Supported by

Project supported by the National Natural Sciences Foundation of China (Nos. 21402116, 21502111), the Key Scientific and Technological Project of Henan Province (No. 172102210099) and the Key Science Research of Education Committee in Henan Province (No. 15A150072).

Fold

Abstract

Transition-metal-catalyzed C-C bond cleavage has been considered as one of the most interesting subject and challenging area in organometallic chemistry. The recent progress of transition-metal-catalyzed (Rh, Ni, Pd and Ru) nitrogen atom chelation-assisted C-C activation and controlled transformation is reviewed, and the mechanisms of these C-C activation reactions are also discussed.

Key words： C-C bond activation; reductive elimination; transition metals; metalation

Cite this article

Wang Jingjing , Li Feng , Yu Xiaobo , Liu Lantao , Ding Junru , Xie Peiyao , Wang Jianhui . Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C-C Bonds Activation Reactions[J]. Chinese Journal of Organic Chemistry, 2018 , 38(7) : 1638 -1649 . DOI: 10.6023/cjoc201802007

References

[1] Reviews/Books on C-C bond or C-H bond activation:
(a) Yu, J. Q.; Shi, Z. J. Topics in Current Chemistry, Springer-Verlag, New York, 2010.
(b) Dong, G. C-C Bond Activation, Springer Verlag, Berlin/Heidelberg, 2014.
(c) Chen, F.; Wang, T.; Jiao, N. Chem. Rev. 2014, 114, 8613.
(d) Dermenci, A.; Coe, J. W.; Dong, G. Org. Chem. Front. 2014, 1, 567.
(e) Liu, H.; Feng, M.; Jiang, X. Chem.-Asian J. 2014, 9, 3360.
(f) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410.
(g) Souillart, L.; Cramer, N. Chem. Rev. 2015, 115, 9410.
(h) Murakami, M.; Chatani, N. Cleavage of Carbon-Carbon Single Bonds by Transition Metals, John Wiley & Sons Ltd., Chichester, U. K., 2016.
(i) Murakami, M.; Ishida, N. J. Am. Chem. Soc. 2016, 138, 13759.
(j) Zheng, Q.-Z.; Jiao, N. Chem. Soc. Rev. 2016, 45, 4590.
(k) Kondo, T. Eur. J. Org. Chem. 2016, 1232.
(l) Murakami, M.; Ishida, N. J. Am. Chem. Soc. 2016, 138, 13759.
(m) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, 117, 8977.
(n) Somerville, R. J.; Martin, R. Angew. Chem., Int. Ed. 2017, 56, 6708.
(o) Yang, J.; Hu, J.; Huang, Y.; Xu, X.; Qing, F. Chin. J. Chem. 2017, 35, 867.
(p) Zhang, J.-R.; Xu, L.; Liao, Y.-Y.; Deng, J.-C.; Tang, R.-Y. Chin. J. Chem. 2017, 35, 271.
(q) Tang, M.-M.; Huo, X.-H.; Meng, Q.-H.; Zhang, W.-B. Acta Chim. Sinica 2016, 74, 219 (in Chinese).
(汤淏溟, 霍小红, 孟庆华, 张万斌, 化学学报, 2016, 74, 219.)
(r) Zhou, Q.-Q.; Liu, D. Xiao, W.-J.; Lu, L.-Q. Acta Chim. Sinica 2017, 75, 110 (in Chinese).
(周泉泉, 刘丹, 肖文精, 陆良秋, 化学学报, 2017, 75, 110.)
(s) Liang, T.-T.; Jiang, L.; Gan, M.-M.; Su, X.; Li, Z.-N. Chin. J. Org. Chem. 2017, 37, 3096 (in Chinese).
(梁婷婷, 姜岚, 干苗苗, 苏鑫, 李争宁, 有机化学, 2017, 37, 3096.)
[2] Bard, A. J.; Whitesides, G. M.; Zare, R. N.; McLaffertv, F. W. Acc. Chem. Res. 1995, 28, 91.
[3] Zhang, L.-H. Advances in Chemical Science, Chemical Industry Press, Beijing, 2005, pp. 85~102 (in Chinese).
(张礼和, 化学学科进展, 化学工业出版社, 北京, pp. 85~102.)
[4] Xu, Z.-J.; Jiao, N. Sci. Sin. Chim. 2013, 43, 1121 (in Chinese).
(许泽君, 焦宁, 中国科学:化学, 2013, 43, 1121.)
[5] Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1984, 106, 3054.
[6] Suggs, J. W.; Jun, C.-H. J. Chem. Soc., Chem. Commun. 1985, 92.
[7] Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J. Angew. Chem., Int. Ed. 2009, 48, 6121.
[8] Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412.
[9] Rathbun, C. M.; Johnson, J. B. J. Am. Chem. Soc. 2011, 133, 2031.
[10] Dennis, J. M.; Compager, C. T.; Dorn, S. K.; Johnson, J. B. Org. Lett. 2016, 18, 3334.
[11] Li, H.; Zhang, X.-S.; Chen, K.; Wang, X. Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244.
[12] Chen, K.; Li, H.; Li, Y.; Zhang, X.-S.; Lei, Z.-Q.; Shi, Z.-J. Chem. Sci. 2012, 3, 1645.
[13] Zhang, X.-S.; Li, Y.; Li, H.; Chen, K.; Lei, Z.-Q.; Shi, Z.-J. Chem. Eur. J. 2012, 18, 16214.
[14] Chen, K.; Li, H.; Lei, Z.-Q.; Li, Y.; Ye, W.-H.; Zhang, L.-S.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2012, 51, 9851.
[15] Lei, Z.-Q.; Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2012, 51, 2690.
[16] Lei, Z.-Q; Pan, F.; Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Li, Y.-X.; Sun, J.; Shi, Z.-J. J. Am. Chem. Soc. 2015, 137, 5012.
[17] Wang, J.; Chen, W.; Zuo, S.; Liu, L.; Zhang, X.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 12334.
[18] (a) Zarghi, A.; Ghodsi, R. Bioorg. Med. Chem. 2010, 18, 5855.
(b) Nien, C.-Y.; Chen, Y.-C.; Kuo, C.-C.; Hsieh, H.-P.; Chang, C.-Y.; Wu, J.-S.; Wu, S.-Y.; Liou, J.-P.; Chang, J.-Y. J. Med. Chem. 2010, 53, 2309.
[19] Thomas, B. C.; James, C. A.; Karol, D. E.; Ulrich, S. WO 2002042248, 2002 [Chem. Abstr. 2002, 137, 6003].
[20] Teruo, O.; Shigeki, S.; Takayuki, I.; Yasuji, U.; Tatsuya, Y.; Noriko, Y. JP 10291988A, 1998 [Chem. Abstr. 1998, 130, 24979].
[21] Yasuo, O.; Juji, N.; Haruki, T.; Naokatsu, S.; Hiroshi, K.; Shunei, Y.; Akio, I. JP 07173138A, 1995 [Chem. Abstr. 1995, 123, 313777].
[22] (a) Dowerah, D.; Radonovich, L. J.; Woolsey, N. F. Organometallics 1990, 9, 614.
(b) Omae, I. Chem. Rev. 1979, 79, 287.
[23] (a) Ueura, K.; Satoh, T.; Miura, M. J. Org. Chem. 2007, 72, 5362.
(b) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 1407.
(c) Kisenyi, J. M.; Sunley, G. J.; Cabeza, J. A.; Smith, A. J.; Adams, H.; Salt, N. J.; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2459.
[24] Wang, J.; Liu, B.; Zhao, H.; Wang, J. Organometallics 2012, 31, 8598.
[25] Lipshutz, B. H.; Frieman, B.; Birkedal, H. Org. Lett. 2004, 6, 2305.
[26] Yu, X. B.; Wang, J. J.; Guo, W. J.; Tian, Y.; Wang, J. Organometallics 2016, 35, 1876.
[27] Zhao, T.-T.; Xu, W.-H.; Zheng, Z.-J.; Xu, P.-F.; Wei, H. J. Am. Chem. Soc. 2018, 140, 586.
[28] Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1999, 121, 8645.
[29] Gribkov, D. V.; Pastine, S. J.; Schnürch, M.; Sames, D. J. Am. Chem. Soc. 2007, 129, 11750.
[30] Niwa, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2007, 46, 2643.
[31] (a) Jun, C.-H.; Lee, H.; Hong, J.-B. J. Org. Chem. 1997, 62, 1200.
(b) Ahn, J.-A.; Chang, D.-H.; Park, Y. J.; Yon, Y. R.; Loupy, A.; Jun, C.-H. Adv. Synth. Catal. 2006, 348, 55.
(c) Lee, D.-Y.; Kim, I.-J.; Jun, C.-H. Angew. Chem., Int. Ed. 2002, 41, 3031.
(d) Jun, C.-H. Chem. Soc. Rev. 2004, 33, 610.
(e) Park, Y. G.; Park, J.-W.; Jun, C.-H. Acc. Chem. Res. 2008, 41, 222.
[32] Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880.
[33] Jun, C.-H.; Lee, D.-Y.; Kim, Y.-H.; Lee, H. Organometallics 2001, 20, 2928.
[34] Jun, C.-H.; Lee, H.; Lim, S.-G. J. Am. Chem. Soc. 2001, 123, 751.
[35] (a) Jun, C.-H.; Hong, J.-B. Org. Lett. 1999, 1, 887.
(b) Jun, C.-H.; Lee, H.; Park, J.-B.; Lee, D.-Y. Org. Lett. 1999, 1, 2161.
(c) Wang, X. M.S. Thesis, Huaibei Normal University, Huaibei, 2014 (in Chinese).
(汪欣, 硕士论文, 淮北师范大学, 淮北, 2014.)
[36] Ahn, J. A.; Chang, D. H.; Park, Y. J.; Yon, Y. R.; Loupy, A.; Jun, C H. Adv. Synth. Catal. 2006, 348, 55.
[37] Vautravers, N. R.; Regent, D. D.; Breit, B. Chem. Commun. 2011, 47, 6635.
[38] Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884.

Options
Outlines

/

〈 〉