Synthesis of 2-Aryl Benzoxazoles from Benzoxazoles and α-Ketoic Acids by Photoredox Catalysis

doi:10.6023/cjoc202110030

Abstract

An efficient protocol for the synthesis of 2-aryl benzoxazoles via visible light-initiation has been developed. Compared with the traditional method for the synthesis of arylbenzoxazole, the reaction conditions of this method are mild, and only Eosin Y is needed as photocatalyst without any other metal catalyst. The purification of the desired product is easier because only CO₂ is produced as the byproduct. Under the optimal reaction conditions, benzoxazole with different substituents and α-keto acids show very good reactivity and a series of arylbenzoxazoles can be synthesized.

Key words: photoredox catalysis, 2-aryl benzoxazole, α-keto acid, radical reaction

Cite this article

Yadong Li, Pengju Wu, Zhiyong Yang. Synthesis of 2-Aryl Benzoxazoles from Benzoxazoles and α-Ketoic Acids by Photoredox Catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1770-1777.

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References 23

[1]	Wei, C.-X.; Guan, L.-P.; Jia, J.-H.; Cha, K.-Y.; Quan, Z.-S. Arch. Pharmacal Res. 2009, 32, 23. doi: 10.1007/s12272-009-1114-4
	(b) Gerova, M.-S.; Stateva, S.-R.; Radonova, E.-M.; Kalenderska, R.-B.; Rusew, R.-I.; Nikolova, R.-P.; Chanev, C.-D.; Shivachev, B.-L.; Apostolova, M.-D.; Petrov, O.-I. Eur. J. Med. Chem. 2016, 120, 121. doi: 10.1016/j.ejmech.2016.05.012
[2]	(a) Seth, K.; Garg, S.-K.; Kumar, R.; Purohit, P.; Meena, V.-S.; Goyal, R.; Banerjee, U.-C.; Chakraborti, A.-K. ACS Med. Chem. Lett. 2014, 5, 512. doi: 10.1021/ml400500e
	(b) Chanda, K.; Rajasekhar, S.; Maiti, B. Synlett 2017, 28, 521. doi: 10.1055/s-0036-1588671
[3]	(a) Abdeen, S.; Kunkle, T.; Salim, N.; Ray, A.-M.; Mammadova, N.; Summers, C.; Stevens, M.; Ambrose, A.-J.; Park, Y.; Schultz, P.-G.; Horwich, A.-L.; Hoang, Q.-Q.; Chapman, E.; Johnson, S.-M. J. Med. Chem. 2018, 61, 7345. doi: 10.1021/acs.jmedchem.8b00989
	(b) Wu, Z.; Bao, X.-L.; Wang, Y.-H.; Anh, N.-T.-P.; Wu, X.-F.; Yan, Y.-J.; Chen, Z.-L. ACS Med. Chem. Lett. 2019, 10, 40. doi: 10.1021/acsmedchemlett.8b00335
[4]	(a) Zhang, W.; Liu, J.; Macho, J.-M.; Jiang, X.; Xie, D.; Jiang, F.; Liu, W.; Fu, L. Eur. J. Med. Chem. 2017, 126, 7. doi: S0223-5234(16)30872-8 pmid: 30525581
	(b) Dementiev, A.; Joachimiak, A.; Nguyen, H.; Gorelik, A.; Illes, K.; Shabani, S.; Gelsomino, M.; Gelsomino, E.-Y.; Ahn, E.; Nagar, B.; Doan, N. J. Med. Chem. 2019, 62, 987. doi: 10.1021/acs.jmedchem.8b01723 pmid: 30525581
[5]	Hantzsch, A.-R.; Weber, J.-H. Eur. J. Inorg. Chem. 187, 20, 3118.
[6]	(a) Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404. doi: 10.1021/ja075802+ pmid: 21744407
	(b) Canivet, J.; Yamaguchi, J.; Ban, I.; Itami, K. Org. Lett. 2009, 11, 1733. doi: 10.1021/ol9001587 pmid: 21744407
	(c) Yamamoto, T.; Muto, K.; Komiyama, M.; Canivet, J.; Yamaguchi, J.; Itami, K. Chem.-Eur. J. 2011, 17, 10113. doi: 10.1002/chem.201101091 pmid: 21744407
	(d) Shibahara, F.; Yamaguchi, E.; Murai, T. Chem. Commun. 2010, 46, 2471. doi: 10.1039/b920794e pmid: 21744407
	(e) Gao, F.; Kim, B.-S.; Walsh, P.-J. Chem. Commun. 2014, 50, 10661. doi: 10.1039/C4CC05307A pmid: 21744407
	(f) Abdellaoui, F.; Youssef, C.; Ammar, H.-B.; Roisnel, T.; Soulé, J.-F.; Doucet, H. ACS Catal. 2016, 6, 4248. doi: 10.1021/acscatal.6b00678 pmid: 21744407
	(g) WangYang, D.; Yu, X.; Fu, H.; Zheng, X.; Chen, H.; Li, R. Chin. J. Org. Chem. 2019, 39, 482. (in Chinese) doi: 10.6023/cjoc201807050 pmid: 21744407
	( 汪洋点点, 余晓军, 付海燕, 郑学丽, 陈华, 李瑞祥, 有机化学, 2019, 39, 482.) doi: 10.6023/cjoc201807050 pmid: 21744407
[7]	(a) Ranjit, S.; Liu, X. Chem.-Eur. J. 2011, 17, 1105. doi: 10.1002/chem.201002787
	(b) Xu, Z.; Wang, Z.; Yu, Z.; Wang, R. Chem.-Eur. J. 2011, 17, 6321. doi: 10.1002/chem.201100136
	(c) Phan, N.-T.-S.; Nguyen, C.-K.; Nguyen, T.-T.; Truong, T. Catal. Sci. Technol. 2014, 4, 369. doi: 10.1039/C3CY00503H
[8]	(a) Xie, K.; Yang, Z.-Y.; Zhou, X.-J.; Li, X.-J.; Wang, S. Z.; Tan, Z.; An, X.-Y.; Guo, C.-C. Org. Lett. 2010, 12, 1564. doi: 10.1021/ol100296b pmid: 26449132
	(b) Yang, K.; Chen, X.; Wang, Y.; Li, W.; Kadi, A.; Fun, H.; Sun, H.; Zhang, Y.; Li, G.; Lu, H. J. Org. Chem. 2015, 80, 11065. doi: 10.1021/acs.joc.5b01450 pmid: 26449132
	(c) Li, Y.; Qian, F.; Wang, M.; Lu, H.; Li, G. Org. Lett. 2017, 19, 5589. doi: 10.1021/acs.orglett.7b02730 pmid: 26449132
	(d) Tian, W.-F.; Hu, C.-H.; He, K.-H.; He, X.-Y.; Li, Y. Org. Lett. 2019, 21, 6930. doi: 10.1021/acs.orglett.9b02539 pmid: 26449132
	(e) Rouchet, J.-B.-E. -Y.; Hachem, M.; Schneider, C.; Hoarau, C. ACS Catal. 2017, 7, 5363. doi: 10.1021/acscatal.7b01330 pmid: 26449132
[9]	(a) Ueda, S.; Nagasawa, H. Angew. Chem., Int. Ed. 2008, 47, 6411. doi: 10.1002/anie.200801240 pmid: 18507387
	(b) Bonnamour, J.; Bolm, C. Org. Lett. 2008, 10, 2665. doi: 10.1021/ol800744y pmid: 18507387
	(c) Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272. doi: 10.1021/jo900513z pmid: 18507387
	(d) Guru, M.-M.; Ali, M.-A.; Punniyamurthy, T. J. Org. Chem. 2011, 76, 5295. doi: 10.1021/jo2005632 pmid: 18507387
	(e) Maleki, B.; Baghayeri, M.; Vahdat, S.-M.; Mohammadzadeh, A.; Akhoondi, S. RSC Adv. 2015, 5, 46545. doi: 10.1039/C5RA06618B pmid: 18507387
[10]	(a) Chen, Y.-X.; Qian, L.-F.; Zhang, W.; Han, B. Angew. Chem. 2008, 47, 9330. doi: 10.1002/anie.200803381 pmid: 31459336
	(b) Cho, Y.-H.; Lee, C.-Y.; Ha, D.-C.; Cheon, C.-H. Adv. Synth. Catal. 2012, 354, 2992. doi: 10.1002/adsc.201200684 pmid: 31459336
	(c) Liu, S.; Chen, R.; Guo, X.; Yang, H.; Deng, G.; Li, C.-J. Green Chem. 2012, 43, 1577. pmid: 31459336
	(d) Yang, Z.; Chen, X.; Wang, S.; Liu, J.; Xie, K.; Wang, A.; Tan, Z. J. Org. Chem. 2012, 77, 7086. doi: 10.1021/jo300740j pmid: 31459336
	(e) Patra, A.; James, A.; Das, T.-K.; Biju, A.-T. J. Org. Chem. 2018, 83, 14820. doi: 10.1021/acs.joc.8b02598 pmid: 31459336
	(f) Nguyen, T. T.; Nguyen, X. T.; Nguyen, T. H.; Tran, P. H. ACS Omega 2019, 4, 368. doi: 10.1021/acsomega.8b02932 pmid: 31459336
	(g) Nguyen, Q. T.; Hang, A.-H. T.; Nguyen, T.-L. H.; Chaua, D.-K. N.; Tran, P. H. RSC Adv. 2018, 8, 11834. doi: 10.1039/C8RA01709C pmid: 31459336
[11]	(a) Foot, J.-S.; Kanno, H.; Giblin, G.-M.-P.; Taylor, R.-J.-K. Synlett 2002, 1291. pmid: 19354284
	(b) Blacker, A.-J.; Farah, M.-M.; Hall, M.-I.; Marsden, S.-P.; Saidi, O.; Williams, J.-M.-J. Org. Lett. 2009, 11, 2039. doi: 10.1021/ol900557u pmid: 19354284
	(c) Wu, M.; Hu, X.; Liu, J.; Liao, Y.; Deng, G.-J. Org. Lett. 2012, 14, 2722. doi: 10.1021/ol300937z pmid: 19354284
[12]	(a) Altenhoff, G.; Glorius, F. Adv. Synth. Catal. 2004, 346, 1661. doi: 10.1002/adsc.200404182
	(b) Viirre, R.-D.; Evindar, G.; Batey, R.-A. J. Org. Chem. 2008, 73, 3452. doi: 10.1021/jo702145d
	(c) Yang, Z.; Wang, A.; Chen, X.; Gui, Q.; Liu, J.; Tan, Z.; Wang, H.; Shi, J.-C. Synlett 2013, 24, 1549. doi: 10.1055/s-0033-1339193
	(d) Endo, Y.; Backvall, J.-E. Chem.-Eur. J. 2012, 18, 13609. doi: 10.1002/chem.201202187
	(e) Nale, D.-B.; Bhanage, B. M. Synlett 2015, 26, 2835. doi: 10.1055/s-0035-1560319
	(f) Zhang, R.; Qin, Y.; Zhang, L. Org. Lett. 2017, 19, 5629. doi: 10.1021/acs.orglett.7b02786
[13]	(a) Hein, D.-M.; Alheim, R. J.; Leavitt, J. J. J. Am. Chem. Soc. 1957, 79, 427. doi: 10.1021/ja01559a053 pmid: 24195716
	(b) Bastug, G.; Eviolitte, C.; Markó, I.-E. Org. Lett. 2012, 14, 3502. doi: 10.1021/ol301472a pmid: 24195716
	(c) Song, Q.; Feng, Q.; Zhou, M. Org. Lett. 2013, 15, 5990. doi: 10.1021/ol402871f pmid: 24195716
	(d) Wang, L.; Ren, X.; Yu, J.; Jiang, Y.; Cheng, J. J. Org. Chem. 2013, 78, 12076. doi: 10.1021/jo402106q pmid: 24195716
	(e) Wang, S.-S.; Fu, H.; Shen, Y.; Sun, M.; Li, Y.-M. J. Org. Chem. 2016, 81, 2920. doi: 10.1021/acs.joc.6b00210 pmid: 24195716
[14]	Yang, Z.; Cheng, Y.; Zhou, L. Chin. J. Synth. Chem. 2020, 28, 84. (in Chinese)
	( 杨志勇, 成园园, 周亮, 合成化学, 2020, 28, 84.)
[15]	(a) Prier, C.-K.; Rankic, D.-A.; MacMillan, D.-W.-C. Chem. Rev. 2013, 113, 5322. pmid: 27070820
	(b) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850. doi: 10.1021/acs.chemrev.5b00662 pmid: 27070820
	(c) Marzo, L.; Pagire, S. K.; Reiser, O.; König, B. Angew. Chem., Int. Ed. 2018, 57, 10034. pmid: 27070820
	(d) Wang, Z.; Li, C.; Domen, K. Chem. Soc. Rev. 2019, 48, 2109. doi: 10.1039/C8CS00542G pmid: 27070820
[16]	(a) Qin, Y.; Zhu, L.; Luo, S. Chem. Rev. 2017, 117, 9433. doi: 10.1021/acs.chemrev.6b00657
	(b) Wang, C.-S.; Dixneuf, P.-H.; Soulé, J.-F. Chem. Rev. 2018, 118, 7532. doi: 10.1021/acs.chemrev.8b00077
	(c) Festa, A.-A.; Voskressensky, L.-G.; Eycken, E.-V.-V. Chem. Soc. Rev. 2019, 48, 4401. doi: 10.1039/C8CS00790J
[17]	(a) Shi, Q.; Li, P.; Zhu, X.; Wang, L. Green Chem. 2016, 18, 4916. doi: 10.1039/C6GC00516K pmid: 30990680
	(b) Xu, W.-T.; Huang, B.; Dai, J.-J.; Xu, J.; Xu, H.-J. Org. Lett. 2016, 18, 3114. doi: 10.1021/acs.orglett.6b01296 pmid: 30990680
	(c) Guo, L.-N.; Wang, H.; Duan, X.-H. Org. Biomol. Chem. 2016, 14, 7380. doi: 10.1039/C6OB01113F pmid: 30990680
	(d) Wang, L.; Wang, Y.; Chen, Q.; He, M. Tetrahedron Lett. 2018, 59, 1489. doi: 10.1016/j.tetlet.2018.03.005 pmid: 30990680
	(e) Raviola, C.; Protti, S.; Ravelli, D.; Fagnoni, M. Green Chem. 2019, 21, 748. doi: 10.1039/C8GC03810D pmid: 30990680
	(f) Penteado, F.; Lopes, E.-F.; Alves, D.; Perin, G.; Jacob, R. G.; Lenardao, E. J. Chem. Rev. 2019, 119, 7113. doi: 10.1021/acs.chemrev.8b00782 pmid: 30990680
[18]	Liu, J.; Liu, Q.; Yi, H.; Qin, C.; Bai, R.; Qi, X.; Lan, Y.; Lei, A. Angew. Chem., Int. Ed. 2014, 53, 502.
[19]	(a) Das, S.; Samanta, S.; Maji, S.-K.; Samanta, P.-K.; Dutta, A.-K.; Srivastava, D. N.; Adhikary, B.; Biswas, P. Tetrahedron Lett. 2012, 54, 1090. doi: 10.1016/j.tetlet.2012.12.044
	(b) Samanta, S.; Das, S.; Biswas, P. J. Org. Chem. 2013, 78, 11184. doi: 10.1021/jo401445j
[20]	Yang, Z.; Zhou, L.; Liu, Y.; Lu, H.; Wu, F.; Xie, Y.; Liu, J. ChemistrySelect 2019, 4, 13788.
[21]	(a) Majek, M.; Filace, F.; Wangelin, A. J. V. Beilstein J. Org. Chem. 2014, 10, 981. doi: 10.3762/bjoc.10.97
	(b) Zhou, C.; Li, P.; Zhu, X.; Wang, L. Org. Lett. 2015, 17, 6198. doi: 10.1021/acs.orglett.5b03192
	(c) Yan, D.; Chen, J.; Xiao, W. Angew. Chem., Int. Ed. 2019, 58, 378. doi: 10.1002/anie.201811102
	(d) Wang, B.; Li, P.; Miao, T.; Zou, L.; Wang, L. Org. Biomol. Chem. 2019, 17, 115. doi: 10.1039/c8ob02476f
	(e) Bosveli, A.; Montagnon, T.; Kalaitzakis, D.; Vassilikogiannakis, G. Org. Biomol. Chem. 2021, 19, 3303. doi: 10.1039/D1OB00301A
[22]	Hari, D.-P.; Schroll, P.; König, B. J. Am. Chem.Soc. 2012, 134, 2958. doi: 10.1021/ja212099r
[23]	Wadhwa, C.; Yang, P. R.; West, K. C.; Deming, S. R. Synth. Commun. 2008, 38, 4434. doi: 10.1080/00397910802369554

Entry	PC	Solvent	Time/h	Yield^b/%
1	Eosin Y	EtOH (dry)	12	42
2	Eosin Y	EtOH/H₂O (2/0.3 mL)	12	55
3	Eosin Y	H₂O	12	0
4	Eosin Y	EtOH/H₂O (2/0.3 mL)	6	56
5	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	60
6	Eosin Y	DMSO/H₂O (2/0.3 mL)	6	0
7	Eosin Y	PhCl/H₂O (2/0.3 mL)	6	0
8	Eosin Y	CH₃CN/H₂O (2/0.3 mL)	6	0
9	Eosin Y	DMF/H₂O (2/0.3 mL)	6	0
10^c	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	8
11^d	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	76
12^e	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	Trace
13	—	MeOH/H₂O (2/0.3 mL)	6	0

Entry	PC	Solvent	Time/h	Yield^b/%
1	Eosin Y	EtOH (dry)	12	42
2	Eosin Y	EtOH/H₂O (2/0.3 mL)	12	55
3	Eosin Y	H₂O	12	0
4	Eosin Y	EtOH/H₂O (2/0.3 mL)	6	56
5	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	60
6	Eosin Y	DMSO/H₂O (2/0.3 mL)	6	0
7	Eosin Y	PhCl/H₂O (2/0.3 mL)	6	0
8	Eosin Y	CH₃CN/H₂O (2/0.3 mL)	6	0
9	Eosin Y	DMF/H₂O (2/0.3 mL)	6	0
10^c	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	8
11^d	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	76
12^e	Eosin Y	MeOH/H₂O (2/0.3 mL)	6	Trace
13	—	MeOH/H₂O (2/0.3 mL)	6	0

可见光催化苯并噁唑与α-酮酸合成芳基苯并噁唑