Research Progress on the Synthesis of Benzofuran Based on Cyclization Strategy

doi:10.6023/cjoc202312027

Abstract

Benzofuran is an essential structural component found in a wide range of natural products, agrochemicals and drugs, possessing a range of biological activities. In recent years, there have been numerous reports of successful syntheses of benzofuran derivatives via intra- and inter-molecular cyclizations using diverse catalysts. This review gives an exhaustive and methodical survey of the procedures for making benzofurans.

Key words: benzofurans, metal-catalyzed reactions, electrochemical reactions, photochemical reactions, mechanistic pathway

Cite this article

Ruiwen Jin, Lianjie Wang, Yue Song, Xiaopei Liu, Junwei Wang, Zhongxian Li. Research Progress on the Synthesis of Benzofuran Based on Cyclization Strategy[J]. Chinese Journal of Organic Chemistry, 2024, 44(9): 2742-2759.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 37

Scheme 1. Biologically active products containing benzofuran structure

Scheme 2. PtCl2-catalyzed the synthesis of benzofurans

Scheme 3. Plausible mechanism of Pt-catalyzed cyclization of o-alkynylphenyl acetals

Scheme 4. Zn(OTf)2-catalyzed the synthesis of benzofurans

Scheme 5. CpRuCl(PPh3)2-catalyzed the synthesis of benzofurans

Scheme 6. Plausible mechanism of CpRuCl(PPh3)2-catalyzed cyclization of aromatic homo- and bis-homopropargylic alcohols

Scheme 7. TiCl3/Zn-catalyzed the synthesis of benzofurans

Scheme 9. Plausible mechanism of CuCl2?2H2O/AgTFA catalyzed the synthesis of benzofurans

Scheme 10. [{Au(IPr)}2-(m-OH)][BF4]/Pb(OAc)2-catalyzed the synthesis of benzofurans

Scheme 11. Rhodium(I)/acid-catalyzed the synthesis of benzofuran derivatives

Scheme 12. Pd(dba)3-catalyzed the synthesis of benzofurans

Scheme 13. Pd2(dba)3/AgOAc-catalyzed the synthesis of benzofurans

Scheme 14. Plausible mechanism of Pd2(dba)3/AgOAc catalyzed the synthesis of benzofurans

Scheme 15. Pd(OAc)2-catalyzed the synthesis of benzofurans

Scheme 16. Plausible mechanism of 3-arylated benzofuran synthesis

Scheme 17. Pd(PPh3)4-catalyzed the synthesis of 7-iodobenzofuran derivatives

Scheme 18. Plausible mechanism for regioselective domino α-arylation/intramolecular O-arylation reaction of 5-substituted-1,2,3-tri- iodobenzene

Scheme 19. Pd(II)-catalyzed the synthesis of benzofuran derivatives

Scheme 20. Plausible mechanism for formation of 2,3-disubstituted benzofuran

Scheme 21. Photochemical synthesis of 2-aryl/alkylbenzofurans

Scheme 22. Plausible mechanism for the synthesis of 2-aryl/alkylbenzofurans

Scheme 23. Visible light catalyzed the synthesis of 2-aryl/alkyl benzofurans

Scheme 24. Plausible mechanism for the synthesis of 2-aryl/alkylbenzofurans

Scheme 25. Ultraviolet (UV) catalyzed the synthesis of 2-aryl/alkyl benzofurans

Scheme 26. Visible-light-induced synthesis of benzofurans

Scheme 27. Dual cobalt and 4CzIPN catalyzed the synthesis of benzofurans under photo irradiation

Scheme 28. Plausible reaction mechanism for the synthesis of benzofurans catalyzed by cobalt and photoredox catalyst under photo irradiation

Scheme 29. Electro-organic synthesis of 2-amino-3-cyano-benzofurans

Scheme 30. Proposed mechanism electro-oxidation of hydroquinones in the presence of malononitrile

Scheme 31. [bmlm]OH catalyzed synthesis of benzofurans

Scheme 32. Plausible mechanism for transformation of o- alkynylphenol into benzofuran activated by [bmIm]OH

Scheme 33. Metal-free BCl3-induced synthesis of benzofurans

Scheme 34. BCl3-induced double borylative cyclization

Scheme 35. Phosphoric acid-catalyzed the synthesis of benzofurans

Scheme 36. Proposed mechanism for the synthesis of benzofurans catalyzed by phosphoric acid

Scheme 37. Iodine-catalyzed the synthesis of benzofurans

Scheme 38. Proposed mechanism for PhI catalyzed cyclization reaction of 2-hydroxystilbenes to 2-arylbenzofurans

References 41

[1]	(a) Pacher, T.; Seger, C.; Engelmeier, D. J. Nat. Prod. 2002, 65, 820. pmid: 12088422
	(b) Kao, C. L.; Chern, J. W. Tetrahedron 2001, 42, 1111. pmid: 12088422
	(c) Akgul, K. K.; Anil, H. Phytochemistry 2003, 63, 939. pmid: 12088422
	(d) Pu, W.; Wang, F.; Wang, C. Chin. J. Org. Chem. 2019, 39, 1277 (in Chinese). pmid: 12088422
	(蒲文臣, 王飞, 王淳, 有机化学, 2019, 39, 1277.) pmid: 12088422
	(e) Oschmann, M.; Holm, L. J.; Pourghasemi-Lati, M.; Verho, O. Molecules 2020, 25, 361. pmid: 12088422
[2]	(a) Zhu, J.; Tian, J. M.; Chen, Y. Y.; Hu, X. J.; Han, X.; Chen, W. C.; Yang, Z. K.; Bao, X. Z.; Ye, X. Y.; Chen, H.; Zhang, F. M.; Wang, H.; Tu, Y. Q. J. Org. Chem. 2023, 88, 14670.
	(b) Khuntia, R.; Mahapatra, S. K.; Roy, L.; Pan, S. C. Chem. Sci. 2023, 14, 10768.
	(c) Cabrera-Pardo1, J. R.; Fuentealba, J.; Gavilá, J.; Cajas, D.; Becerra, J.; Napiórkowska, M. Front. Pharmacol. 2020. 10. 1679.
[3]	(a) Pieters, L.; Van, D. S.; Gao, M. J. Med. Chem. 1999, 42, 5475. pmid: 11130670
	(b) Pauletti, P. M.; Araujo, A. R.; Young, M. C. Phytochemistry 2000, 55, 597. pmid: 11130670
	((c) Zhao, Y.; Liu, W.; Sun, X.; Lin, G. Chin. J. Org. Chem. 2012, 32, 1919 (in Chinese). pmid: 11130670
	(赵云辉, 刘文杰, 孙兴文, 林国强, 有机化学, 2019, 39, 456.) pmid: 11130670
[4]	(a) Joule, A.; Smit, G. F. Heterocyclic Chemistry, 3rd ed., London, CRC Press, 1995, p. 536.
	(b) Tan, Y. X.; Yang, Y.; Zhang, T. Fitoterapia 2010, 87, 742.
	(c) Carey, F. A.; Sundberg, R. A. Advanced Organic Chemistry, Science Publishing Company, New York, 2007, pp. 759-762.
[5]	Nakamura, I.; Mizushima, Y.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022. pmid: 16248630
[6]	Kumar, M. P.; Liu, R. S. J. Org. Chem. 2006, 71, 4951.
[7]	Varela-Fernández, A.; González-Rodríguez, C.; Varela, J. A. Org. Lett. 2009, 11, 5350. doi: 10.1021/ol902212h pmid: 19860408
[8]	Jumbam, N. D.; Yedwa, M.; Masamba, W. Bull. Chem. Soc. Ethiop. 2011, 25, 157.
[9]	Li, H.; Liu, G. J. Org. Chem. 2014, 79, 509.
[10]	Oonishi, Y.; Gomez-Suarez, A.; Martin, A. R. Chem. Eur. J. 2014, 20, 13507.
[11]	Zhu, H. L.; Zhou, Q. Q.; Liu, N. Xing, J. H.; Yao, W. J.; Dou, X. W. Adv. Synth. Catal. 2022, 364, 1162.
[12]	Guilarte, V.; Castroviejo, M. P.; Álvarez, Beilstein, E. J. Org. Chem. 2011, 7, 1255.
[13]	Kuram, M. R.; Bhanuchandra, M.; Sahoo, A. K. Angew. Chem., Int. Ed. 2013, 52, 4607.
[14]	Agasti, S.; Sharma, U.; Naveen, T.; Maiti, D. Chem. Commun. 2015, 51, 5375.
[15]	Al-Zoubi, R. M.; Al-Jammal, W. K.; Ferguson, M. J. RSC Adv. 2021, 11, 30069. doi: 10.1039/d1ra05730h pmid: 35493993
[16]	Reddy, R. J.; Sharadha, N.; Krishna, G. R. J. Org. Chem. 2023, 88, 8889.
[17]	Ghosh, S.; Das, J. Tetrahedron Lett. 2011, 52, 1112.
[18]	Ghosh, S.; Das, J.; Saikh. F. Tetrahedron Lett. 2012, 53, 5883.
[19]	Protti, S.; Fagnoni, M.; Albini, A. J. Org. Chem. 2012, 77, 6473.
[20]	Zhang, L.; Si, X.; Rominger, F.; Hashmi, A. S. K. J. Am. Chem. Soc. 2020, 142, 10485.
[21]	Zhu, Y.; He, Y. Q.; Tian, W. F.; Wang, M.; Zhou, Z. Z.; Song, X. R.; Ding, H. X.; Xiao, Q. Adv. Synth. Catal. 2021, 363, 3372.
[22]	Zhao, J.; Nguyen, S. C.; Ye, R.; Ye, B.; Weller, H.; Somorjai, G. A.; Alivisatos, A. P.; Toste, F. D. ACS Cent. Sci. 2017, 3, 482.
[23]	Fakhari, A. R.; Ahmar, H. Synth. Commun. 2011, 41, 561.
[24]	Siddiqui, I. R.; Waseem, M. A.; Shamim, S. Tetrahedron Lett. 2013, 54, 4154.
[25]	Warner, A. J.; Churn, A.; McGough, J. S. Angew. Chem., Int. Ed. 2016, 56, 354.
[26]	Ma, W.; Huang, J.; Huang, X. Org. Chem. Front. 2019, 6, 493.
[27]	Mangaonkar, S. R.; Shetgaonkar, S. E.; Vernekar, A. A. ChemistrySelect 2020, 5, 107541.
[28]	Du, W. Q.; Yang, R. J.; Wu, J. W.; Xia, Z. H. Eur. J. Org. Chem. 2023, 26, e202201497.
[29]	Li, Y. K.; Tung, C. H.; Xu, Z. H. Org. Lett. 2022, 24, 5829.
[30]	Hashmi, A. S. K.; Yang, W.; Rominger, F. Angew. Chem., Int. Ed. 2011, 50, 5762.
[31]	Oschmann, M.; Holm, L. J.; Lati, M. P. Molecules 2020, 25, 361.
[32]	Cabrera-Pardo, J. R.; Fuentealba, J.; Gavilán, J. Front. Pharmacol. 2019, 10, 1679. doi: 10.3389/fphar.2019.01679 pmid: 32082168
[33]	Kumar, A.; Kumar, M.; Verma, A. K. J. Org. Chem. 2020, 85, 13983. doi: 10.1021/acs.joc.0c02024 pmid: 33064481
[34]	Zhang, B. B.; Li, X. M.; Li, X. X.; Yu, Z. Y.; Zhao, B. Y.; Wang, X. F.; Du, Y. F.; Zhao, K. J. Org. Chem. 2021, 86, 17274.
[35]	Geary, L. M.; Hultin, P. G. Org. Lett. 2009, 11, 5478.
[36]	Hu, Z. Y.; Dong, J. H.; Li, Z. Y.; Yuan, B.; Wei, R.Y.; Xu, X. X. Org. Lett. 2018, 20, 6750.
[37]	Abu-Hashem, A. A.; Hussein, H. A. R.; Aly, A. S.; Gouda, M. A. Synth. Commun. 2014, 44, 2285.
[38]	Heravi, M. M.; Zadsirjan, V. Heterocycl. Chem. 2015, 117, 261.
[39]	Zhang, W.; Xu, W.; Zhang, F.; Li, Y. Chin. J. Org. Chem. 2019, 39, 1277 (in Chinese).
	(张文生, 许文静, 张斐, 李焱, 有机化学, 2019, 39, 1277.) doi: 10.6023/cjoc201811023
[40]	Huang, J.; Fu, R.; Jing, L.; Qin, D.; Huang, K.; Wang, W. Chin. J. Org. Chem. 2019, 39, 456 (in Chinese).
	(黄锦, 付荣辉, 敬林海, 秦大斌, 黄昆, 汪伟, 有机化学, 2019, 39, 456.) doi: 10.6023/cjoc201807040
[41]	Naveen, T. Tetrahedron 2021, 84, 132025.

基于成环策略构建苯并呋喃的合成研究