Progress in Transition-Metal-Catalyzed Cyclization of Carbodiimides

doi:10.6023/cjoc202010020

Abstract

Carbodiimide is one of the most efficient precursors to the synthesis of N-containing molecules. Transition-metal- catalyzed cyclization of carbodiimides has become a powerful approach to heterocyclic products, and attracts considerable attention from synthetical and pharmaceutical chemists. The significant amount of documents that were published during the last years proves the importance of this approach in modern organic synthesis. The development of this field over last decade and some pioneering work are summarized. An array of synthetic methods for privileged heterocycles from carbodiimides are presented according to mechanically distinctive processes: cascade cyclization initiated by nucleophilic process, catalytic cyclization via the insertion of carbodiimides into metal-cycle intermediates and annulation of tethered carbodiimides with unsaturated systems.

Key words: carbodiimide, transition-metal-catalysis, cyclization, heterocycle, heterocumulene

Cite this article

Zhen Zhang, Wenxu Chang. Progress in Transition-Metal-Catalyzed Cyclization of Carbodiimides[J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1835-1850.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 43

Scheme 1. Transition-metal-catalyzed cyclization of carbodiimides via distinctive paths

Scheme 2. Strategy of cascade cyclization with group in carbodiimide

Scheme 3. Cu(I)-catalyzed cascade cyclization to synthesize 2-heterobenzimidazoles

Scheme 4. Cu(II)-catalyzed cascade cyclization to synthesize benzimidazoles or quinazolines

Scheme 5. Ag(I)-catalyzed regioselective cyclization to synthesize indole N-carboximidamides or N-carboximidoates

Scheme 6. Cu(I)-catalyzed one-pot synthesis of 2-azolylimidazole derivatives

Scheme 7. Tandem Pd-catalyzed addition/cyclocarbonylation to synthesize 2-heteroquinazolin-4(3H)-ones

Scheme 8. Pd-catalyzed three-component reaction to synthesize quinazolin-4(3H)-imines and 4-imino-3,4-dihydroquinazolin-2- ylphosphonates

Scheme 9. Strategy of cascade cyclization with the functional group in nucleophile

Scheme 10. Pd(0)-catalyzed cycloaddition of vinyloxiranes with carbodiimides

Scheme 11. Pd-catalyzed cyclization to synthesize 2-vinyl- aziridines or 2-vinylpyrrolidines with carbodiimides

Scheme 12. Ligand-free Cu(I)-catalyzed cascade reaction of o-halophenols or o-haloanilines with carbodiimides

Scheme 13. Cu-catalyzed domino reaction of carbodiimides and benzoic acid derivatives

Scheme 14. Cu(I)-catalyzed domino reaction of α-hydroxy- ketones and carbodiimide to synthesize 2-imino-1,3-oxazoline

Scheme 15. Pd-catalyzed cyclocarbonylation of o-iodoanilines with carbodiimides

Scheme 16. Zn(OTf)2-catalyzed guanylation/amidation of amino acid esters and carbodiimides

Scheme 17. Zn(OTf)2, La[N(SiMe3)2]3 and imidazolin-2-iminato titanium initiator catalyzed guanylation/cyclization

Scheme 18. Cu-catalyzed cascade annulation of carbodiimides, alkynes and diaryliodonium salts

Scheme 19. Sequential Pd(0)/Fe(III)-catalyzed coupling/cycli- zation to synthesize aminotetrazoles in one-pot fashion

Scheme 20. Strategy of cascade cyclization with the functional group in both carbodiimide and nucleophile

Scheme 21. Pd-catalyzed cascade cyclization of carbodiimides, amines with CO or isocyanides

Scheme 22. Cu(I)-catalyzed tandem reaction of carbodiimides and isocyanoacetates

Scheme 23. Cu(I)-catalyzed domino reaction of bis(o-haloaryl)carbodiimides and azole derivatives

Scheme 24. Cu(I)-catalyzed domino reaction of bis-(o-haloaryl)carbodiimides and active methylene compounds

Scheme 25. Cu(I)-catalyzed domino reaction of o-haloarylcarbodiimides and propargylic amines

Scheme 26. Cu(I)-catalyzed cascade reaction of o-alkenylphenyl carbodiimides with isocyanides

Scheme 27. Co or Ni-catalyzed cyclotrimerization of acetylenes with carbodiimides

Scheme 28. Co-catalyzed microwave-mediated solid-supported formation of fused pyridine rings

Scheme 29. Rh-catalyzed [2+2+2] cycloaddition of diynes with carbodiimides

Scheme 30. Rh-catalyzed [4+2] annulations of 4-alkynals with carbodiimides

Scheme 31. Fe(CO)5-catalyzed [2+2+1] cycloaddition of alkyne, carbodiimide and CO

Scheme 32. Ni-catalyzed decarboxylative cyclization of isatoic anhydrides with carbodiimides

Scheme 33. Rh-catalyzed [2+2+2] cycloaddition of pentenyl carbodiimides with terminal alkynes

Scheme 34. Rh-catalyzed cascade reaction of vinyl azides with isonitriles and alkynes/benzynes

Scheme 35. Rh-catalyzed double isocyanides insertion via a vinylcarbodiimide intermediate

Scheme 36. Pd-catalyzed intramolecular carboborylation of car- bodiimides bearing 1,3-diene

Scheme 37. General process of catalytic Aza-Pauson-Khand reaction of alkyne carbodiimide with CO

Scheme 38. Transition-metal-mediated intramolecular alkyne- carbodiimide Pauson-Khand-type reaction

Scheme 39. Co2(CO)8-catalyzed intramolecular Pauson-Khand- type reaction of alkyne carbodiimide for the synthesis of (±)- physostigmine

Scheme 40. Rh(I)-catalyzed Pauson-Khand-type reaction of alkyne carbodiimide to synthesize pyrrolo[2,3-b]quinolines

Scheme 41. Rh(I)-catalyzed intramolecular [2+2+2] cycloaddition of bis(propargylphenyl)-carbodiimides

Scheme 42. Rh(I)-catalyzed “ene-type” cycloisomerization of N-[2-(2-alkyn-1-yl)phenyl] carbodiimides

Scheme 43. Self-relay Rh(I)-catalyzed cyclization of alkyne-azides with two σ-donor/π-acceptor (isonitriles or CO)

References 51

[1]	(a) Vovk, M. V.; Samarai, L. I. Russ. Chem. Rev. 1992, 61, 297. doi: 10.1070/RC1992v061n03ABEH000946
	(b) Williams, A.; Ibrahim, I. T. Chem. Rev. 1981, 81, 589. doi: 10.1021/cr00046a004
	(c) Ulrich, H. Chemistry and Technology of Carbodiimides, John Wiley & Sons, Ltd, Chichester, UK, 2007.
[2]	(a) Zhang, W. X.; Hou, Z. Org. Biomol. Chem. 2008, 6, 1720. doi: 10.1039/b800135a pmid: 24626874
	(b) Alonso-Moreno, C.; Antinolo, A.; Carrillo-Hermosilla, F.; Otero, A. Chem. Soc. Rev. 2014, 43, 3406. doi: 10.1039/c4cs00013g pmid: 24626874
	(c) Xu, L.; Zhang, W.-X.; Xi, Z. Organometallics 2015, 34, 1787. doi: 10.1021/acs.organomet.5b00251 pmid: 24626874
	(d) Zhang, W.-X.; Xu, L.; Xi, Z. Chem. Commun. 2015, 51, 254. doi: 10.1039/C4CC05291A pmid: 24626874
	(e) Wang, L.; Chi, Y.; Zhang, W.; Xi, Z. Chin. J. Org. Chem. 2018, 38, 1341. (in Chinese). doi: 10.6023/cjoc201801037 pmid: 24626874
	(王连军, 迟樾, 张文雄, 席振峰, 有机化学, 2018, 38, 1341.) doi: 10.6023/cjoc201801037 pmid: 24626874
[3]	Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkov, A. A.; Van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3861. doi: 10.1039/C7CS00065K
[4]	Wang, Y.; Zhang, W. X.; Xi, Z. Chem. Soc. Rev. 2020, 49, 5810. doi: 10.1039/C9CS00478E
[5]	Lv, X.; Bao, W. J. Org. Chem. 2009, 74, 5618. doi: 10.1021/jo900743y
[6]	(a) Evindar, G.; Batey, R. A. Org. Lett. 2003, 5, 133. pmid: 12529123
	(b) Yang, T.; Lin, C.; Fu, H.; Jiang, Y.; Zhao, Y. Org. Lett. 2005, 7, 4781. doi: 10.1021/ol052126c pmid: 12529123
[7]	He, H.-F.; Wang, Z.-J.; Bao, W. Adv. Synth. Catal. 2010, 352, 2905. doi: 10.1002/adsc.v352.17
[8]	Huang, N. Y.; Liu, M. G.; Ding, M. W. J. Org. Chem. 2009, 74, 6874. doi: 10.1021/jo901362c
[9]	Lin, Y.; Li, E.; Wu, X.; Wang, L.; Wang, H.; Li, X.; Kang, H.; Zhou, L.; Shen, G.; Lv, X. Org. Biomol. Chem. 2020, 18, 1476. doi: 10.1039/C9OB02532D
[10]	(a) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2012, 113, 1. doi: 10.1021/cr300100s
	(b) Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Rev. 2015, 115, 5301. doi: 10.1021/cr5006974
[11]	Zeng, F.; Alper, H. Org. Lett. 2010, 12, 1188. doi: 10.1021/ol902924x
[12]	(a) Domling, A. Chem. Rev. 2006, 106, 17. doi: 10.1021/cr0505728
	(b) Lygin, A. V.; de Meijere, A. Angew. Chem., nt. Ed. 2010, 49, 9094.
[13]	Qiu, G.; Liu, G.; Pu, S.; Wu, J. Chem. Commun. 2012, 48, 2903. doi: 10.1039/c2cc18001d
[14]	Qiu, G.; Lu, Y.; Wu, J. Org. Biomol. Chem. 2013, 11, 798. doi: 10.1039/C2OB26979A
[15]	Larksarp, C.; Alper, H. J. Org. Chem. 1998, 63, 6229. doi: 10.1021/jo9804341
[16]	(a) Butler, D. C.; Inman, G. A.; Alper, H. J. Org. Chem. 2000, 65, 5887. doi: 10.1021/jo000608q
	(b) Zhou, H.-B.; Alper, H. Tetrahedron 2004, 60, 73. doi: 10.1016/j.tet.2003.10.088
[17]	Wang, F.; Cai, S.; Liao, Q.; Xi, C. J. Org. Chem. 2011, 76, 3174. doi: 10.1021/jo200014v
[18]	Shen, G.; Bao, W. Adv. Synth. Catal. 2010, 352, 981. doi: 10.1002/adsc.201000022
[19]	Duangjan, C.; Rukachaisirikul, V.; Saithong, S.; Kaeobamrung, J. Tetrahedron Lett. 2018, 59, 3537.
[20]	Han, M.-S.; Hahn, H.-G. Bull. Korean Chem. Soc. 2012, 33, 1371. doi: 10.5012/bkcs.2012.33.4.1371
[21]	Larksarp, C.; Alper, H. J. Org. Chem. 2000, 65, 2773. doi: 10.1021/jo991922r
[22]	Chi, Y.; Xu, L.; Du, S.; Yan, H.; Zhang, W. X.; Xi, Z. Chem.-Eur. J. 2015, 21, 10369.
[23]	Lu, C.; Gong, C.; Zhao, B.; Hu, L.; Yao, Y. J. Org. Chem. 2018, 83, 1154. doi: 10.1021/acs.joc.7b02550
[24]	Das, S.; Bhattacharjee, J.; Panda, T. K. Dalton Trans. 2019, 48, 7227. doi: 10.1039/C8DT04630A
[25]	Chi, Y.; Yan, H.; Zhang, W. X.; Xi, Z. Org. Lett. 2017, 19, 2694. doi: 10.1021/acs.orglett.7b01025
[26]	Pathare, R. S.; Ansari, A. J.; Verma, S.; Maurya, A.; Maurya, A. K.; Agnihotri, V. K.; Sharon, A.; Pardasani, R. T.; Sawant, D. M. J. Org. Chem. 2018, 83, 9530. doi: 10.1021/acs.joc.8b01261
[27]	Zeng, F.; Alper, H. Org. Lett. 2010, 12, 3642. doi: 10.1021/ol101428v
[28]	Qiu, G.; He, Y.; Wu, J. Chem. Commun. 2012, 48, 3836. doi: 10.1039/c2cc30928a
[29]	Qiu, G.; Wu, J. Chem. Commun. 2012, 48, 6046. doi: 10.1039/c2cc32135a
[30]	Yuan, G.; Liu, H.; Gao, J.; Yang, K.; Niu, Q.; Mao, H.; Wang, X.; Lv, X. J. Org. Chem. 2014, 79, 1749. doi: 10.1021/jo402742k
[31]	Xu, B.; Peng, B.; Cai, B.; Wang, S.; Wang, X.; Lv, X. Adv. Synth. Catal. 2016, 358, 653. doi: 10.1002/adsc.201500455
[32]	Hao, W.; Sang, X.; Xiao, Y.; Cai, M. Tetrahedron Lett. 2016, 57, 4207. doi: 10.1016/j.tetlet.2016.08.006
[33]	Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 18, 1333. doi: 10.1016/S0040-4039(01)93010-2
[34]	Hoberg, H.; Burkhart, G. Synthesis 1979, 1979, 525. doi: 10.1055/s-1979-28743
[35]	Young, D. D.; Deiters, A. Angew. Chem., nt. Ed. 2007, 46, 5187.
[36]	Ishii, M.; Mori, F.; Tanaka, K. Chem.-Eur. J. 2014, 20, 2169.
[37]	Tanaka, K.; Mimura, M.; Hojo, D. Tetrahedron 2009, 65, 9008. doi: 10.1016/j.tet.2009.06.115
[38]	Raghuvanshi, A.; Singh, A. K.; Mobin, S. M.; Mathur, P. ChemistrySelect 2017, 2, 9245. doi: 10.1002/slct.201701625
[39]	Zhang, Z.; Qin, Z.; Chang, W.; Li, J.; Fan, R.; Wu, X.; Guo, R.; Xie, X.; Zhou, L. Adv. Synth. Catal. 2020, 362, 2864. doi: 10.1002/adsc.v362.14
[40]	Lee, E. E.; Rovis, T. Org. Lett. 2008, 10, 1231. doi: 10.1021/ol800086s
[41]	Li, Z.; Huo, T.; Li, L.; Feng, S.; Wang, Q.; Zhang, Z.; Pang, S.; Zhang, Z.; Wang, P.; Zhang, Z. Org. Lett. 2018, 20, 7762. doi: 10.1021/acs.orglett.8b03115
[42]	Wang, Y.; Li, Z.; Zhao, H.; Zhang, Z. Synthesis 2019, 51, 3250. doi: 10.1055/s-0037-1611830
[43]	Tsukano, C.; Nakajima, M.; Hande, S. M.; Takemoto, Y. Org. Biomol. Chem. 2019, 17, 1731. doi: 10.1039/C8OB02224K
[44]	Saito, T.; Shiotani, M.; Otani, T.; Hasaba, S. Heterocycles 2003,60.
[45]	Saito, T.; Sugizaki, K.; Otani, T.; Suyama, T. Org. Lett. 2007, 9, 1239. doi: 10.1021/ol063123i
[46]	Mukai, C.; Yoshida, T.; Sorimachi, M.; Odani, A. Org. Lett. 2006, 8, 83. doi: 10.1021/ol052562z
[47]	Saito, T.; Furukawa, N.; Otani, T. Org. Biomol. Chem. 2010, 8, 1126. doi: 10.1039/b924301a
[48]	Otani, T.; Saito, T.; Sakamoto, R.; Osada, H.; Hirahara, A.; Furukawa, N.; Kutsumura, N.; Matsuo, T.; Tamao, K. Chem. Commun. 2013, 49, 6206. doi: 10.1039/c3cc42792g
[49]	Tateno, K.; Ogawa, R.; Sakamoto, R.; Tsuchiya, M.; Kutsumura, N.; Otani, T.; Ono, K.; Kawai, H.; Saito, T. J. Org. Chem. 2018, 83, 690. doi: 10.1021/acs.joc.7b02674
[50]	Otani, T.; Onishi, M.; Seino, T.; Furukawa, N.; Saito, T. RSC Adv. 2014, 4, 53669. doi: 10.1039/C4RA11846D
[51]	Zhang, Z.; Xiao, F.; Huang, B.; Hu, J.; Fu, B.; Zhang, Z. Org. Lett. 2016, 18, 908. doi: 10.1021/acs.orglett.5b03570

过渡金属催化碳二亚胺环化的研究进展