Recent Advances in the Synthesis of Ynamides

doi:10.6023/cjoc202107051

Abstract

Ynamides are a class of special ynamines bearing an electron-withdrawing group on the nitrogen atom. The electron-withdrawing group endows ynamides an optimal balance between the stability and activity, and thus enabling ynamides to be versatile synthons widely used in organic synthetic chemistry. The ynamide chemistry has witnessed a rapid development over the past two decades. As a consequence, its synthetic methods have attracted widespread attention. In this context, the recent advances in the synthesis of ynamides are reviewed herein. According to the structure of the main starting materials, the contents are classified as the synthesis with haloenamides, alkynes or its derivatives, and dihalo-substituted alkenes. The representative mechanisms are also discussed.

Key words: ynamide, electron-withdrawing group, internal ynamide, terminal ynamide

Cite this article

Yongli Zhao, Yongliang Tu, Mingzhong Cai, Junfeng Zhao. Recent Advances in the Synthesis of Ynamides[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 85-99.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 50

Scheme 1. The first synthesis of ynamine

Scheme 2. Structure of ynamides

Scheme 3. The first synthesis of ynamide

Scheme 4. The first synthesis of terminal ynamides

Scheme 5. Synthesis of ynamides via elimination reaction

Scheme 6. Synthesis of ynamides with formamides

Scheme 7. Synthesis of ynamides with trichloroethene

Scheme 8. Synthesis of ynamides by Suzuki-Miyaura coupling

Scheme 9. Synthesis of ynamides with alkynyl iodonium salts

Scheme 10. Synthesis of ynamides with alkynyl iodonium salt and the possible mechanism

Scheme 11. Synthesis of highly functionalized ynamides

Scheme 12. Synthesis of ynamides containing an alkynyl group

Scheme 13. The first synthesis of chiral ynamides

Scheme 14. Synthesis of chiral α-branched ynamides

Scheme 15. Metal-free synthesis of ynamides

Scheme 16. Synthesis of ynamides with PIDA as oxidant

Scheme 17. Synthesis of ynamides with EBX-MeCN complex

Scheme 18. Synthesis of ynamides with hypervalent alkynyl iodine reagents and application of leucine-derived ynamide

Scheme 19. The first synthesis of internal ynamides by copper catalysis and proposed mechanism

Scheme 20. Cu-mediated synthesis of ynamides

Scheme 21. Synthesis of ynamides by copper zeolite (USY) catalysis

Scheme 22. The first synthesis of ynamide by Fe catalysis

Scheme 23. Synthesis of ynamides by APGS-550-M catalysis

Scheme 24. Synthesis of N-phosphoryl ynamides

Scheme 25. Synthesis of N-alkynyl sulfoximines

Scheme 26. Synthesis of S-perfluoro alkynyl sulfoximines

Scheme 27. Synthesis of ynamides containing oxazolidinone or carbamate by CuCN catalysis

Scheme 28. CuI catalyzed N-alkynylation of sulphonamides

Scheme 29. Copper-mediated N-alkynylation of carbamates

Scheme 30. Synthesis of ynamides with the combination of Cu-salt and 1,10-phen

Scheme 31. Synthesis of multi-ynamides by CuSO4 catalysis

Scheme 32. (a) Oxidative amidation and (b) proposed mechanism of propiolic acids

Scheme 33. Synthesis of N-alkynyl sulfoximines by oxidative decarboxylation coupling

Scheme 34. Synthesis of ynamides with alkynylboron reagents and amides

Scheme 35. Synthesis of ynamides by oxidative coupling with alkynylcopper reagents

Scheme 36. The first synthesis of N-alkynyl imides

Scheme 37. Synthesis of ynamides by transition metal catalysis

Scheme 38. Synthesis of ynamides by oxidative amidation of alkynes

Scheme 39. Synthesis of ynamides by oxidative cross-coupling with copper hydroxide

Scheme 40. (a) Synthesis of ynamides by CuO mediated oxidative coupling and (b) proposed mechanism

Scheme 41. Synthesis of ynehydrazides

Scheme 42. Synthesis of N-alkynyl sulfoximines by oxidative coupling of alkynes

Scheme 43. Synthesis of ynamides with 1,1-dibromo-1-alkenes

Scheme 44. Proposed mechanism

Scheme 45. Selective synthesis of ynamides and 1,1-dienamides

Scheme 46. Synthesis of ynamides with imidazoles and pyrazoles

Scheme 47. Synthesis of ynamides with 1,2-dibromo-1-styrenes

Scheme 48. Synthesis of ynamides with 2-bromo-1-iodoalkenes

Scheme 49. Synthesis of ynediamides

Scheme 50. One step synthesis of ynamides with 1,1- or 1,2- dichloroalkenes

References 67

[1]	Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575. doi: 10.1016/S0040-4020(01)00681-0
[2]	Zaugg, H.; Swett, L.; Stone, G. J. Org. Chem. 1958, 23, 1389. doi: 10.1021/jo01103a617
[3]	(a) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.; Zhang, Y.; Hsung, R. P. Chem. Rev. 2010, 110, 5064. doi: 10.1021/cr100003s pmid: 20429503
	(b) Evano, G.; Coste, A.; Jouvin, K. Angew. Chem., nt. Ed. 2010, 49, 2840. pmid: 20429503
[4]	(a) Lynch, C. C.; Sripada, A.; Wolf, C. Chem. Soc. Rev. 2020, 49, 8543. doi: 10.1039/D0CS00769B
	(b) Luo, J.; Chen, G.-S.; Chen, S.-J.; Yu, J.-S.; Li, Z.-D.; Liu, Y.-L. ACS Catal. 2020, 10, 13978. doi: 10.1021/acscatal.0c04180
	(c) Li, X.; Jiang, M.; Zhan, T.; Cao, W.; Feng, X. Chem Asian J. 2020, 15, 1953. doi: 10.1002/asia.v15.13
	(d) Ito, T.; Harada, S.; Homma, H.; Takenaka, H.; Hirose, S.; Nemoto, T. J. Am. Chem. Soc. 2021, 143, 604. doi: 10.1021/jacs.0c10682
	(e) Li, X.; Zeng, H.; Lin, L.; Feng, X. Org. lett. 2021, 23, 2954. doi: 10.1021/acs.orglett.1c00631
	(f) Zhu, B.-H.; Zhang, Y.-Q.; Xu, H.-J.; Li, L.; Deng, G.-C.; Qian, P.-C.; Deng, C.; Ye, L.-W. ACS Catal. 2021, 11, 1706. doi: 10.1021/acscatal.0c04786
[5]	(a) Zhou, B.; Tan, T.-D.; Zhu, X.-Q.; Shang, M.; Ye, L.-W. ACS Catal. 2019, 9, 6393. doi: 10.1021/acscatal.9b01851 pmid: 32483965
	(b) Li, X.; Sun, Y.; Zhang, L.; Peng, B. Chin. J. Org. Chem. 2016, 36, 2530. (in Chinese) doi: 10.6023/cjoc201605046 pmid: 32483965
	(李晓锦, 孙艳, 张磊, 彭勃, 有机化学, 2016, 36, 2530.) doi: 10.6023/cjoc201605046 pmid: 32483965
	(c) Debrauwer, V.; Turlik, A.; Rummler, L.; Prescimone, A.; Blanchard, N.; Houk, K. N.; Bizet, V. J. Am. Chem. Soc. 2020, 142, 11153. doi: 10.1021/jacs.0c03556 pmid: 32483965
	(d) An, D.; Zhang, W.; Pan, B.; Zhao, Y. Eur. J. Org. Chem. 2020, 2021, 314. pmid: 32483965
	(e) Chen, Z.; Nie, X. D.; Sun, J. T.; Yang, A. M.; Wei, B. G. Org. Biomol. Chem. 2021, 19, 2492. doi: 10.1039/D0OB02603D pmid: 32483965
	(f) Gao, E.; Peng, C.; Zhang, J.; Wang, X. N.; Chang, J. Org. Biomol. Chem. 2021, 19, 2182. doi: 10.1039/D0OB02575E pmid: 32483965
	(g) Nie, X. D.; Han, X. L.; Sun, J. T.; Si, C. M.; Wei, B. G.; Lin, G. Q. J. Org. Chem. 2021, 86, 3433. doi: 10.1021/acs.joc.0c02807 pmid: 32483965
	(h) Sarathkumar, S.; Kavala, V.; Yao, C. F. Org. lett. 2021, 23, 1960. doi: 10.1021/acs.orglett.0c04068 pmid: 32483965
[6]	(a) Wang, X. N.; Yeom, H. S.; Fang, L. C.; He, S.; Ma, Z. X.; Kedrowski, B. L.; Hsung, R. P. Acc. Chem. Res. 2014, 47, 560. doi: 10.1021/ar400193g
	(b) Pan, F.; Shu, C.; Ye, L. W. Org. Biomol. Chem. 2016, 14, 9456. doi: 10.1039/C6OB01774F
	(c) Duret, G.; Le Fouler, V.; Bisseret, P.; Bizet, V.; Blanchard, N. Eur. J. Org. Chem. 2017, 6816.
	(d) Zhou, X.; Liang, Z.; Wang, X.-N. Chin. J. Org. Chem. 2021, 41, 1288. (in Chinese) doi: 10.6023/cjoc202009025
	(周欣悦, 梁宗显, 王晓娜, 有机化学, 2021, 41, 1288.) doi: 10.6023/cjoc202009025
	(e) Ye, L.-W.; Li, L.; Luo, W.-F. Synlett 2021, 32, 1302.
	(f) Chen, Y. B.; Qian, P. C.; Ye, L. W. Chem. Soc. Rev. 2020, 49, 8897. doi: 10.1039/D0CS00474J
	(g) Liao, Y.; Zhu, L.; Yu, Y.; Chen, G.; Huang, X. Chin. J. Org. Chem. 2017, 37, 2785. (in Chinese) doi: 10.6023/cjoc201708021
	(廖云, 朱磊, 俞颖华, 陈贵, 黄学良, 有机化学, 2017, 37, 2785.) doi: 10.6023/cjoc201708021
	(h) Zhu, C.; Feng, J.; Zhang, J. Chin. J. Org. Chem. 2017, 37, 1165. (in Chinese) doi: 10.6023/cjoc201701043
	(朱超泽, 冯见君, 张俊良, 有机化学, 2017, 37, 1165.) doi: 10.6023/cjoc201701043
	(i) Liu, X.; Liu, X.; Ye, L. Chin. J. Org. Chem. 2021, 41, 1207. (in Chinese) doi: 10.6023/cjoc202009020
	(刘晓涛, 刘鑫, 叶龙武, 有机化学, 2021, 41, 1207.) doi: 10.6023/cjoc202009020
[7]	Hu, Y. C.; Zhao, Y.; Wan, B.; Chen, Q. A. Chem. Soc. Rev. 2021, 50, 2582. doi: 10.1039/D0CS00283F
[8]	(a) Evano, G.; Michelet, B.; Zhang, C. C. R. Chim. 2017, 20, 648. doi: 10.1016/j.crci.2016.12.002
	(b) Li, L.; Tan, T.-D.; Zhang, Y.-Q.; Liu, X.; Ye, L.-W. Org. Biomol. Chem. 2017, 15, 8483. doi: 10.1039/C7OB01895A
	(c) Hong, F. L.; Ye, L. W. Acc. Chem. Res. 2020, 53, 2003. doi: 10.1021/acs.accounts.0c00417
[9]	(a) Mahe, C.; Cariou, K. Adv. Synth. Catal. 2020, 362, 4820. doi: 10.1002/adsc.v362.22
	(b) Tan, T. D.; Wang, Z. S.; Qian, P. C.; Ye, L. W. Small Method 2020, 5, 2000673. doi: 10.1002/smtd.v5.3
	(c) Deng, Y.; Zhang, J.; Bankhead, B.; Markham, J. P.; Zeller, M. Chem. Commun. 2021, 57, 5254. doi: 10.1039/D1CC02016A
	(d) Zeng, L.; Jin, J.; He, J.; Cui, S. Chem. Commun. 2021, 57, 6792. doi: 10.1039/D1CC02559G
	(e) Zhou, G.; Su, J.; Shang, T.; Wang, X.; Bai, Y.; Yuan, Z.; Zhu, G. Org. Chem. Front. 2021, 8, 4473. doi: 10.1039/D1QO00559F
[10]	(a) Evano, G.; Jouvin, K.; Coste, A. Synthesis 2012, 45, 17. doi: 10.1055/s-00000084 pmid: 33356269
	(b) Cook, A. M.; Wolf, C. Tetrahedron Lett. 2015, 56, 2377. doi: 10.1016/j.tetlet.2015.03.111 pmid: 33356269
	(c) Evano, G.; Blanchard, N.; Compain, G.; Coste, A.; Demmer, C. S.; 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. doi: 10.1246/cl.160260 pmid: 33356269
	(d) Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459. doi: 10.1016/S0040-4020(00)01014-0 pmid: 33356269
	(e) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379. pmid: 33356269
	(f) Zhao, L.; Yang, H.; Li, R.; Tao, Y.; Guo, X. F.; Anderson, E. A.; Whiting, A.; Wu, N. J. Org. Chem. 2021, 86, 1938. doi: 10.1021/acs.joc.0c02326 pmid: 33356269
[11]	Janousek, Z.; Collard, J.; Viehe, H. G., Angew. Chem., nt. Ed. 1972, 11, 917.
[12]	Joshi, R. V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089.
[13]	Brückner, D. Tetrahedron 2006, 62, 3809. doi: 10.1016/j.tet.2005.11.091
[14]	Rodríguez, D.; Castedo, L, Saá, C. Synlett 2004, 783.
[15]	Rodríguez, D.; Martínez-Esperón, M.; Castedo, L, Saá, C. Synlett 2007, 1963.
[16]	Mansfield, S. J.; Campbell, C. D.; Jones, M. W.; Anderson, E. A. Chem. Commun. 2015, 51, 3316.
[17]	Mansfield, S. J.; Smith, R. C.; Yong, J. R. J.; Garry, O. L.; Anderson, E. A. Org. Lett. 2019, 21, 2918. doi: 10.1021/acs.orglett.9b00971 pmid: 30942600
[18]	Couty, S.; Barbazanges, M.; Meyer, C.; Cossy, J. Synlett 2005, 905.
[19]	Murch, P.; Williamson, B. L.; Stang, P. J. Synthesis 1994, 1255.
[20]	(a) Witulski, B.; Stengel, T. Angew. Chem., nt. Ed. 1998, 37, 489.
	(b) Witulski, B.; Gossmann, M. Synlett 2000, 1793.
[21]	(a) Witulski, B.; Schweikert, T.; Schollmeyer, D.; Nemkovich, N. A. Chem. Commun. 2010, 46, 2953. doi: 10.1039/b919275a
	(b) Witulski, B.; Lumtscher, J.; Bergsträßer, U. Synlett 2003, 708.
	(c) Witulski, B.; Stengel, T. Angew. Chem., nt. Ed. 1999, 38, 242.
[22]	(a) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272. pmid: 11076583
	(b) Rainier, J. D.; Imbriglio, J. E. Org. Lett. 1999, 1, 2037. doi: 10.1021/ol9912128 pmid: 11076583
[23]	Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440. doi: 10.1021/jo9605814
[24]	Witulski, B.; Gößmann, M. Chem. Commun. 1999, 1879.
[25]	Souto, J. A.; Becker, P.; Iglesias, A.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 15505. pmid: 22909000
[26]	Xiang, D.; Li, H.; Zhang, L.; Zhang, Y.; Zhang, Q.; Li, D. Asian J. Org. Chem. 2019, 8, 537. doi: 10.1002/ajoc.201900110
[27]	Yudasaka, M.; Shimbo, D.; Maruyama, T.; Tada, N.; Itoh, A. Org. Lett. 2019, 21, 1098. doi: 10.1021/acs.orglett.9b00005
[28]	Takai, R.; Shimbo, D.; Tada, N.; Itoh, A. J. Org. Chem. 2021, 86, 4699. doi: 10.1021/acs.joc.1c00101
[29]	Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368. pmid: 12603105
[30]	(a) Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C.; Vera, E. L. Org. Lett. 2004, 6, 1151. doi: 10.1021/ol049827e
	(b) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170. doi: 10.1021/jo060230h
[31]	Hsung., R. P. Org. Synth. 2007, 84, 359. doi: 10.15227/orgsyn.084.0359
[32]	Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Adv. Synth. Catal. 2006, 348, 2437. doi: 10.1002/(ISSN)1615-4169
[33]	Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011. doi: 10.1021/ol035647d
[34]	Kohnen, A. L. Org. Synth. 2007, 84, 88. doi: 10.15227/orgsyn.084.0088
[35]	Harkat, H.; Borghèse, S.; Nigris, M. D.; Kiselev, S.; Bénéteau, V.; Pale, P. Adv. Synth. Catal. 2014, 356, 3842. doi: 10.1002/adsc.v356.18
[36]	Yao, B.; Liang, Z.; Niu, T.; Zhang, Y. J. Org. Chem. 2009, 74, 4630. doi: 10.1021/jo900595c
[37]	Yang, Y.; Meng, X.; Zhu, B.; Jia, Y.; Cao, X.; Huang, S. Eur. J. Org. Chem. 2019, 1166.
[38]	DeKorver, K. A.; Walton, M. C.; North, T. D.; Hsung, R. P. Org. Lett. 2011, 13, 4862. doi: 10.1021/ol201947b pmid: 21848304
[39]	Chen, X. Y.; Wang, L.; Frings, M.; Bolm, C. Org. Lett. 2014, 16, 3796. doi: 10.1021/ol5016898
[40]	Anselmi, E.; Le, T. N.; Bouvet, S.; Diter, P.; Pégot, B.; Magnier, E. Eur. J. Org. Chem. 2016, 4423.
[41]	(a) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727. pmid: 14986960
	(b) Hirano, S.; Fukudome, Y.; Tanaka, R.; Sato, F.; Urabe, H. Tetrahedron 2006, 62, 3896. doi: 10.1016/j.tet.2005.11.080 pmid: 14986960
[42]	(a) Amanda, L. Kohnen, J. R. D. and Rick, L. Danheiser, R. L. Org. Synth. 2007, 84, 88. doi: 10.15227/orgsyn.084.0088
	(b) Wang, Y. P.; Danheiser, R. L. Tetrahedron Lett. 2011, 52, 2111. doi: 10.1016/j.tetlet.2010.11.002
[43]	Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681. pmid: 16092849
[44]	Betou, M.; Sallustrau, A.; Toupet, L.; Trolez, Y. Tetrahedron Lett. 2015, 56, 4627. doi: 10.1016/j.tetlet.2015.06.027
[45]	Jia, W.; Jiao, N. Org. Lett. 2010, 12, 2000. doi: 10.1021/ol1004615
[46]	Priebbenow, D. L.; Becker, P.; Bolm, C. Org. Lett. 2013, 15, 6155. doi: 10.1021/ol403106e pmid: 24280013
[47]	Jouvin, K.; Couty, F.; Evano, G. Org. Lett. 2010, 12, 3272. doi: 10.1021/ol101322k pmid: 20565123
[48]	Jouvin, K.; Heimburger, J.; Evano, G. Chem. Sci. 2012, 3, 756. doi: 10.1039/C2SC00842D
[49]	Sueda, T.; Oshima, A.; Teno, N. Org. Lett. 2011, 13, 3996. doi: 10.1021/ol2014973
[50]	Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A.; Domiano, P. Tetrahedron Lett. 1985, 26, 4141. doi: 10.1016/S0040-4039(00)89314-4
[51]	Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833. doi: 10.1021/ja077406x
[52]	Jin, X.; Yamaguchi, K.; Mizuno, N. Chem. Commun. 2012, 48, 4974. doi: 10.1039/c2cc31159c
[53]	Tong, X.; Ni, G.; Deng, X.; Xia, C. Synlett 2012, 23, 2497. doi: 10.1055/s-00000083
[54]	Beveridge, R. E.; Batey, R. A. Org. Lett. 2012, 14, 540. doi: 10.1021/ol2031608 pmid: 22216967
[55]	Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F. F.; Bolm, C. Angew. Chem., nt. Ed. 2013, 52, 3478.
[56]	(a) Evano, G.; Lecomte, M.; Thilmany, P.; Theunissen, C. Synthesis 2017, 49, 3183. doi: 10.1055/s-0036-1588452
	(b) Guissart, C.; Luhmer, M.; Evano, G. Tetrahedron 2018, 74, 6727. doi: 10.1016/j.tet.2018.09.053
[57]	Coste, A.; Karthikeyan, G.; Couty, F.; Evano, G. Angew. Chem., nt. Ed. 2009, 48, 4381.
[58]	Coste, A.; Couty, F.; Evano, G. Org. Lett. 2009, 11, 4454. doi: 10.1021/ol901831s
[59]	Das, B.; Salvanna, N.; Reddy, G. C.; Balasubramanyam, P. Tetrahedron Lett. 2011, 52, 6497. doi: 10.1016/j.tetlet.2011.09.117
[60]	Yang, Y.; Zhang, X.; Liang, Y. Tetrahedron Lett. 2012, 53, 6557. doi: 10.1016/j.tetlet.2012.09.092
[61]	Xue, J.; Luo, M.-T.; Wen, Y.-L.; Ye, M.; Liu, L.-X.; Chen, Z.-W. Synthesis 2014, 46, 3191. doi: 10.1055/s-00000084
[62]	Mansfield, S. J.; Christensen, K. E.; Thompson, A. L.; Ma, K.; Jones, M. W.; Mekareeya, A.; Anderson, E. A. Angew. Chem., nt. Ed. 2017, 56, 14428.
[63]	Hu, L.; Xu, S.; Zhao, Z.; Yang, Y.; Peng, Z.; Yang, M.; Wang, C.; Zhao, J. J. Am. Chem. Soc. 2016, 138, 13135. doi: 10.1021/jacs.6b07230
[64]	(a) Yang, J.; Wang, C.; Xu, S.; Zhao, J. Angew. Chem., nt. Ed. 2019, 58, 1382.
	(b) Yang, J.; Wang, C.; Yao, C.; Chen, C.; Hu, Y.; He, G.; Zhao, J. J. Org. Chem. 2020, 85, 1484. doi: 10.1021/acs.joc.9b02486
[65]	Yao, C.; Yang, J.; Lu, X.; Zhang, S.; Zhao, J. Org. lett. 2020, 22, 6628. doi: 10.1021/acs.orglett.0c02402
[66]	(a) Yang, M.; Wang, X.; Zhao, J. ACS Catal. 2020, 10, 5230. doi: 10.1021/acscatal.0c00523
	(b) Wang, X.; Yang, Y.; Zhao, Y.; Wang, S.; Hu, W.; Li, J.; Wang, Z.; Yang, F.; Zhao, J. J. Org. Chem. 2020, 85, 6188. doi: 10.1021/acs.joc.0c00485
[67]	(a) Xu, S.; Zhao, Z.; Zhao, J. Chin. Chem. Lett. 2018, 29, 1009. doi: 10.1016/j.cclet.2018.05.024
	(b) Liu, T.; Xu, S.; Zhao, J. Chin. J. Org. Chem. 2021, 41, 873. (in Chinese) doi: 10.6023/cjoc202011022
	(刘涛, 许泗林, 赵军锋, 有机化学, 2021, 41, 873.) doi: 10.6023/cjoc202011022
	(a) Tu, Y.; Zeng, X.; Wang, H.; Zhao, J. Org. Lett. 2018, 20, 280. doi: 10.1021/acs.orglett.7b03665
	(b) Zeng, X.; Tu, Y.; Zhang, Z.; You, C.; Wu, J.; Ye, Z.; Zhao, J. J. Org. Chem. 2019, 84, 4458. doi: 10.1021/acs.joc.8b03192

炔酰胺合成方法研究进展