Download PDF
Synlett 2024; 35(02): 155-159
DOI: 10.1055/a-2103-9720
synpacts

Synthesis of Ynamides by C(sp)–H Amidation

Xiaolan Xie
a   College of Chemical Engineering and Materials Science, Quanzhou Normal University, Quanzhou 362000, P. R. of China
,
Na Hou
a   College of Chemical Engineering and Materials Science, Quanzhou Normal University, Quanzhou 362000, P. R. of China
,
Yan Lin
b   School of Special Education, Quanzhou Normal University, Quanzhou 362000, P. R. of China
,
Jian Lei  ∗
a   College of Chemical Engineering and Materials Science, Quanzhou Normal University, Quanzhou 362000, P. R. of China
› Author AffiliationsFinancial support was received from the National Natural Science Foundation of China (21702120), the Natural Science Foundation of Fujian Province (2021J01965, 2018Y0073), Quanzhou City Science and Technology Program of China (2019C021R), and the Program for the Cultivation of Outstanding Young Scientific Talents in Fujian Province University.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Ynamides are versatile reactive building blocks in organic chemistry; consequently, synthetic methodologies to fabricate these compounds have received extensive attention. The construction of a C–N bond between an alkyne surrogate and an amide is a powerful and practical way to access ynamides, and has been widely studied. Recently, the amidation of terminal alkynes has emerged as a straightforward alternative. This Synpacts article briefly summarizes the use of C(sp)–H amidation strategies to form ynamides; it also highlights our recent work on the synthesis of ynehydrazides through the copper-catalyzed addition of terminal alkynes to dialkyl azodicarboxylates. Finally, some future directions in this field are outlined.

Key words

ynamides - alkynes - copper catalysis - ynehydrazides - azodicarboxylates


Publication History

Received: 11 May 2023

Accepted after revision: 31 May 2023

Accepted Manuscript online:
31 May 2023

Article published online:
12 July 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References


      • For key comprehensive reviews, see:
    • 1a DeKorver KA, Li H, Lohse AG, Hayashi R, Lu Z, Zhang Y, Hsung RP. Chem. Rev. 2010; 110: 5064
      CrossrefPubMed
    • 1b Evano G, Coste A, Jouvin K. Angew. Chem. Int. Ed. 2010; 49: 2840
      CrossrefPubMed

      For reviews on the synthesis of ynamides, see:
    • 2a Evano G, Jouvin K, Coste A. Synthesis 2013; 45: 17
      Article in Thieme Connect
    • 2b Cook AM, Wolf C. Tetrahedron Lett. 2015; 56: 2377
      CrossrefPubMed
    • 2c Evano G, Blanchard N, Compain G, Coste A, Demmer CS, Gati W, Guissart C, Heimburger J, Henry N, Jouvin K, Karthikeyan G, Laouiti A, Lecomte M, Martin-Mingot A, Métayer B, Michelet B, Nitelet A, Theunissen C, Thibaudeau S, Wang J, Zarca M, Zhang C. Chem. Lett. 2016; 45: 574
      Crossref
    • 2d Zhao Y, Tu Y, Cai M, Zhao J. Youji Huaxue 2022; 42: 85; (in Chinese)
    • 2e Mulder JA, Kurtz KC. M, Hsung RP. Synlett 2003; 1379

      For selected reviews, see:
    • 3a Wang X.-N, Yeom H.-S, Fang L.-C, He S, Ma Z.-X, Kedrowski BL, Hsung RP. Acc. Chem. Res. 2014; 47: 560
      CrossrefPubMed
    • 3b Duret G, Le Fouler V, Bisseret P, Bizet V, Blanchard N. Eur. J. Org. Chem. 2017; 6816
      Crossref
    • 3c Prabagar B, Ghosh N, Sahoo AK. Synlett 2017; 28: 2539
      Article in Thieme Connect
    • 3d Evano G, Michelet B, Zhang C. C. R. Chim. 2017; 20: 648
      CrossrefPubMed
    • 3e Dodd RH, Cariou K. Chem. Eur. J. 2018; 24: 2297
      CrossrefPubMed
    • 3f Chen Y.-B, Qian P.-C, Ye L.-W. Chem. Soc. Rev. 2020; 49: 8897
      CrossrefPubMed
    • 3g Mahea C, Cariou K. Adv. Synth. Catal. 2020; 362: 4820
      Crossref
    • 3h Lynch CC, Sripada A, Wolf C. Chem. Soc. Rev. 2020; 49: 8543
      CrossrefPubMed
    • 3i Zhou X, Liang Z, Wang X.-N. Youji Huaxue 2021; 41: 1288 ; (in Chinese)
    • 4a Hamada T, Ye X, Stahl SS. J. Am. Chem. Soc. 2008; 130: 833
      CrossrefPubMed
    • 4b Jin X, Yamaguchi K, Mizuno N. Chem. Commun. 2012; 48: 4974
      CrossrefPubMed
    • 4c Laouiti A, Rammah MM, Rammah MB, Marrot J, Couty F, Evano G. Org. Lett. 2012; 14: 6
      CrossrefPubMed
    • 4d Wang L, Huang H, Priebbenow DL, Pan F.-F, Bolm C. Angew. Chem. Int. Ed. 2013; 52: 3478
      CrossrefPubMed
  • 5 Souto JA, Becker P, Iglesias Á, Muñiz K. J. Am. Chem. Soc. 2012; 134: 15505
    CrossrefPubMed
  • 6 Lavernhe R, Torres-Ochoa RO, Wang Q, Zhu J. Angew. Chem. Int. Ed. 2021; 60: 24028
    CrossrefPubMed
    • 7a Lei J, Gao H, Huang M, Liu X, Mao Y, Xie X. Chem. Commun. 2020; 56: 920
      CrossrefPubMed
    • 7b Lei J, Xie W, Li J, Wu Y, Xie X. Eur. J. Org. Chem. 2021; 2021: 4364
      Crossref
    • 8a Diana-Rivero R, Halsvik B, Tellado FG, Tejedor D. Org. Lett. 2021; 23: 4078
      CrossrefPubMed
    • 8b Walker PR, Campbell CD, Suleman A, Carr G, Anderson EA. Angew. Chem. Int. Ed. 2013; 52: 9139
      CrossrefPubMed
    • 8c Campbell CD, Greenaway RL, Holton OT, Walker PR, Chapman HA, Russell CA, Carr G, Thomson AL, Anderson EA. Chem. Eur. J. 2015; 21: 12627
      CrossrefPubMed
    • 8d Chen J, Palani V, Hoye TR. J. Am. Chem. Soc. 2016; 138: 4318
      CrossrefPubMed
    • 8e Zhang C, Blanchard N, Evano G. Synthesis 2023; 55: 272
      Article in Thieme Connect
    • 8f Tuck JR, Tombari RJ, Yardeny N, Olson DE. Org. Lett. 2021; 23: 4305
      CrossrefPubMed
  • 9 Denonne F, Seiler P, Diederich F. Helv. Chim. Acta 2003; 86: 3096
    Crossref
    • 11a Uemura T, Chatani N. J. Org. Chem. 2005; 70: 8631
      CrossrefPubMed
    • 11b Kisseljova K, Tšubrik O, Sillard R, Mäeorg S, Mäeorg U. Org. Lett. 2006; 8: 43
      CrossrefPubMed
    • 11c Gu L, Neo BS, Zhang Y. Org. Lett. 2011; 13: 1872
      CrossrefPubMed
    • 12a Hay AS. J. Org. Chem. 1962; 27: 3320
      CrossrefPubMed
    • 12b Siemsen P, Livingston RC, Diederich F. Angew. Chem. Int. Ed. 2000; 39: 2632
      CrossrefPubMed
  • 13 Yang Z, Wang B, Xu X, Wang H, Li X. Youji Huaxue 2015; 35: 207 (in Chinese)
    CrossrefPubMed
  • 14 Lei J, Sha W, Xie X, Weng W.-T. Org. Lett. 2023; 25: 320
    CrossrefPubMed
    • 15a Pfaff P, Anderl F, Fink M, Balkenhohl M, Carreira EM. J Am. Chem. Soc. 2021; 143: 14495
      CrossrefPubMed
    • 15b Fang D, Zhang Z.-Y, Shangguan Z, He Y, Yu C, Li T. J. Am. Chem. Soc. 2021; 143: 14502
      CrossrefPubMed
    • 15c Huang SJ, Paneccasio V, DiBattista F, Picker D, Wilson G. J. Org. Chem. 1975; 40: 124
      Crossref
  • 16 He C, Chen C, Cheng J, Liu C, Liu W, Li Q, Lei A. Angew. Chem. Int. Ed. 2008; 47: 6414
    CrossrefPubMed