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SCIENCE CHINA Chemistry, Volume 60, Issue 11: 1413-1424(2017) https://doi.org/10.1007/s11426-017-9025-1

Ni-mediated C–N activation of amides and derived catalytic transformations

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  • ReceivedJan 20, 2017
  • AcceptedFeb 20, 2017
  • PublishedMay 5, 2017

Abstract

Amide, as a ubiquitous functional group, is essential in various aspects of chemistry and biology. Although the history of studying amide is rich and fruitful, the synthetic application of amide is very limited due to the inertness of amide C–N bond. Recently, significant advances have been achieved towards the nickel-mediated C–N activation of amides. This approach allows a facile generation of acyl-nickel intermediates, and a number of unique transformations have been designed and realized based on the amide C–N bond activation. Focused on the catalytic transformation, this review summarizes and categorizes the recent advances on the synthetic applications of Ni-mediated C–N bond activation of amides.


Funded by

Zhejiang University and Chinese “Thousand Youth Talents Plan”.


Acknowledgment

This work was supported by Zhejiang University and the Chinese “Thousand Youth Talents Plan”.


Interest statement

The authors declare that they have no conflict of interest.


References

[1] Greenberg A, Breneman CM, Liebman JF. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science. New York: John Wiley & Sons, 2003. Google Scholar

[2] Zhu RY, Farmer ME, Chen YQ, Yu JQ. Angew Chem Int Ed, 2016, 55: 10578-10599 CrossRef PubMed Google Scholar

[3] Meng G, Shi S, Szostak M, Dander JE, Garg NK, Liu C, Szostak M. Synlett, 2016, 27: 2530-2540 CrossRef Google Scholar

[4] Meng G, Szostak M, Liu C, Meng G, Szostak M, Meng G, Szostak M, Liu C, Meng G, Liu Y, Liu R, Lalancette R, Szostak R, Szostak M, Meng G, Szostak M, Meng G, Shi S, Szostak M. Angew Chem Int Ed, 2015, 54: 14518-14522 CrossRef PubMed Google Scholar

[5] Li X, Zou G, Li X, Zou G, Cui M, Wu H, Jian J, Wang H, Liu C, Daniel S, Zeng Z, Wu H, Li Y, Cui M, Jian J, Zeng Z. Chem Commun, 2015, 51: 5089-5092 CrossRef PubMed Google Scholar

[6] Meng G, Szostak M, Wu H, Liu T, Cui M, Li Y, Jian J, Wang H, Zeng Z. Org Lett, 2016, 18: 796-799 CrossRef PubMed Google Scholar

[7] Li Z, Zhang SL, Fu Y, Guo QX, Liu L, Li Z, Liu L, Hong X, Liang Y, Houk KN. J Am Chem Soc, 2009, 131: 8815-8823 CrossRef PubMed Google Scholar

[8] Weires NA, Baker EL, Garg NK. Nat Chem, 2016, 8: 75–79. Google Scholar

[9] Liu LL, Chen P, Sun Y, Wu Y, Chen S, Zhu J, Zhao Y. J Org Chem, 2016, 81: 11686-11696 CrossRef PubMed Google Scholar

[10] Szostak R, Aubé J, Szostak M, Szostak R, Shi S, Meng G, Lalancette R, Szostak M, Pace V, Holzer W, Meng G, Shi S, Lalancette R, Szostak R, Szostak M, Szostak R, Aubé J, Szostak M, Szostak M, Aubé J. Chem Commun, 2015, 51: 6395-6398 CrossRef PubMed Google Scholar

[11] Liu Y, Meng G, Liu R, Szostak M. Chem Commun, 2016, 52: 6841-6844 CrossRef PubMed Google Scholar

[12] Shi S, Meng G, Szostak M. Angew Chem Int Ed, 2016, 55: 6959-6963 CrossRef PubMed Google Scholar

[13] Simmons BJ, Weires NA, Dander JE, Garg NK. ACS Catal, 2016, 6: 3176-3179 CrossRef Google Scholar

[14] Shi S, Szostak M. Org Lett, 2016, 18: 5872-5875 CrossRef PubMed Google Scholar

[15] Shi S, Szostak M. Chem Eur J, 2016, 22: 10420-10424 CrossRef PubMed Google Scholar

[16] Hie L, Fine Nathel NF, Shah TK, Baker EL, Hong X, Yang YF, Liu P, Houk KN, Garg NK. Nature, 2015, 524: 79-83 CrossRef PubMed ADS Google Scholar

[17] Hie L, Baker EL, Anthony SM, Desrosiers JN, Senanayake C, Garg NK. Angew Chem Int Ed, 2016, 55: 15129-15132 CrossRef PubMed Google Scholar

[18] Baker EL, Yamano MM, Zhou Y, Anthony SM, Garg NK. Nat Commun, 2016, 7: 11554 CrossRef PubMed ADS Google Scholar

[19] Hu J, Zhao Y, Liu J, Zhang Y, Shi Z. Angew Chem Int Ed, 2016, 55: 8718-8722 CrossRef PubMed Google Scholar

[20] Dey A, Sasmal S, Seth K, Lahiri GK, Maiti D. ACS Catal, 2017, 7: 433-437 CrossRef Google Scholar

[21] Tobisu M, Nakamura K, Chatani N. J Am Chem Soc, 2014, 136: 5587-5590 CrossRef PubMed Google Scholar

[22] Lei Y, Wrobleski AD, Golden JE, Powell DR, Aubé J. J Am Chem Soc, 2005, 127: 4552-4553 CrossRef PubMed Google Scholar

[23] Hu F, Lalancette R, Szostak M. Angew Chem Int Ed, 2016, 55: 5062-5066 CrossRef PubMed Google Scholar

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