Visible Light-Induced Hydroxyalkylation of Heteroarenes with Aliphatic Alcohols

doi:10.6023/cjoc202112032

Abstract

An efficient visible light-induced direct cross-dehydrogenative coupling of heteroarenes with aliphatic alcohols in aqueous solution at ambient temperature was developed. The reaction is initiated by persulfate salts and does not require the use of stoichiometric acid for activation of the heterocycle. α-Hydroxyalkyl radicals transiently generated from alcohols via hydrogen atom transfer (HAT) undergo Minisci-type reactions with a range of heteroarenes. This protocol was highlighted by photocatalyst-free, green solvent, mild conditions, readily available starting materials, and wide functional group tolerance.

Key words: alcohol, cross-dehydrogenative coupling, heteroarene, hydroxyalkylation, visible light-induction

Cite this article

Dongping Xu, Fei Huang, Lin Tang, Xinming Zhang, Wu Zhang. Visible Light-Induced Hydroxyalkylation of Heteroarenes with Aliphatic Alcohols[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1493-1500.

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References 17

[1]	(a) Proctor, R. S. J.; Phipps, R. J. Angew. Chem., Int. Ed. 2019, 58, 13666. doi: 10.1002/anie.201900977
	(b) Evano, G.; Theunissen, C. Angew. Chem., Int. Ed. 2019, 58, 7558. doi: 10.1002/anie.201806631
	(c) Xu, P.; Chen, P. Y.; Xu, H. C. Angew. Chem., Int. Ed. 2020, 59, 14275. doi: 10.1002/anie.202005724
[2]	(a) Shang, X. J.; Liu, Z. Q. Chem. Soc. Rev. 2013, 42, 3253. doi: 10.1039/c2cs35445d
	(b) Xia, X.; Li, L.; Liang, Y. Chin. J. Org. Chem. 2013, 33, 675. (in Chinese) doi: 10.6023/cjoc201301019
	(夏晓峰, 李莲花, 梁永民, 有机化学, 2013, 33, 675.) doi: 10.6023/cjoc201301019
	(c) Zhang, Y.; Feng, B. Chin. J. Org. Chem. 2014, 34, 2406. (in Chinese) doi: 10.6023/cjoc201408030
	(张艳, 冯柏年, 有机化学, 2014, 34, 2406.) doi: 10.6023/cjoc201408030
	(d) Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74. doi: 10.1002/anie.201304268
	(e) Liu, C.; Yuan, J. W.; Gao, M.; Tang, S.; Li, W.; Shi, R. Y.; Lei, A. W. Chem. Rev. 2015, 115, 12138. doi: 10.1021/cr500431s
	(f) Liu, S. H.; Liu, A. X.; Zhang, Y. Q.; Wang, W. Chem. Sci. 2017, 8, 4044. doi: 10.1039/C6SC05697K
	(g) Yang, Q.; Zhang, L.; Ye, C.; Luo, S. Z.; Wu, L. Z.; Tung, C. H. Angew. Chem., Int. Ed. 2017, 56, 3694. doi: 10.1002/anie.201700572
	(h) Tian, H. T.; Yang, H.; Tian, C.; An, G. H.; Li, G. M. Org. Lett. 2020, 22, 7709. doi: 10.1021/acs.orglett.0c02912
	(i) Dong, J.; Liu, Y.; Wang, Q. Chin. J. Org. Chem. 2021, 41, 3771. (in Chinese) doi: 10.6023/cjoc202104024
	(董建洋, 刘玉秀, 汪清民, 有机化学, 2021, 41, 3771.)
[3]	(a) Yi, H.; Zhang, G. T.; Wang, H. M.; Huang, Z. Y.; Wang, J.; Singh, A. K.; Lei, A. W. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
	(b) Wang, H. M.; Gao, X. L.; Lv, Z. C.; Abdelilah, T.; Lei, A. W. Chem. Rev. 2019, 119, 6769. doi: 10.1021/acs.chemrev.9b00045
[4]	(a) Jin, L. K.; Wan, L.; Feng, J.; Cai, C. Org. Lett. 2015, 17, 4726. doi: 10.1021/acs.orglett.5b02217 pmid: 28970941
	(b) Lakshman, M. K.; Vuram, P. K. Chem. Sci. 2017, 8, 5845. doi: 10.1039/c7sc01045a pmid: 28970941
[5]	Jin, S.; Xie, B.; Lin, S.; Min, C.; Deng, R.; Yan, Z. Org. Lett. 2019, 21, 3436. doi: 10.1021/acs.orglett.9b01212
[6]	(a) Fu, J.; Yuan, J.; Zhang, Y.; Xiao, Y.; Mao, P.; Diao, X.; Qu, L. Org. Chem. Front. 2018, 5, 3382. doi: 10.1039/C8QO00979A
	(b) Yang, J.; Xie, D.; Zhou, H.; Chen, S.; Duan, J.; Huo, C.; Li, Z. Adv. Synth. Catal. 2018, 360, 3471. doi: 10.1002/adsc.201800467
[7]	Jagadeesh, R. V.; Junge, H.; Pohl, M. M.; Radnik, J.; Brückner, A.; Beller, M. J. Am. Chem. Soc. 2013, 135, 10776. doi: 10.1021/ja403615c
[8]	(a) Li, C.; Liu, R. Y.; Jesikiewicz, L. T.; Yang, Y.; Liu, P.; Buchwald, S. L. J. Am. Chem. Soc. 2019, 141, 5062. doi: 10.1021/jacs.9b01784
	(b) Fuse, H.; Nakao, H.; Saga, Y.; Fukatsu, A.; Kondo, M.; Masaoka, S.; Mitsunuma, H.; Kanai, M. Chem. Sci. 2020, 11, 12206. doi: 10.1039/D0SC04114A
[9]	(a) Xu, W. X.; Dai, X. Q.; Weng, J. Q. ACS Omega 2019, 4, 11285. doi: 10.1021/acsomega.9b01695 pmid: 31460231
	(b) Niu, L. B.; Liu, J. M.; Liang, X. A.; Wang, S. C.; Lei, A. W. Nat. Commun. 2019, 10, 467. doi: 10.1038/s41467-019-08413-9 pmid: 31460231
[10]	(a) Wu, X. X.; Zhang, H.; Tang, N. N.; Wu, Z.; Wang, D. P.; Ji, M. S.; Xu, Y.; Wang, M.; Zhu, C. Nat. Commun. 2018, 9, 3343. doi: 10.1038/s41467-018-05522-9
	(b) Wang, M.; Yin, C. Z.; Hu, P. Org. Lett. 2021, 23, 722. doi: 10.1021/acs.orglett.0c03944
[11]	(a) Correia, C. A.; Yang, L.; Li, C. J. Org. Lett. 2011, 13, 4581. doi: 10.1021/ol201774b
	(b) He, T.; Yu, L.; Zhang, L.; Wang, L.; Wang, M. Org. Lett. 2011, 13, 5016. doi: 10.1021/ol201779n
	(c) Kianmehr, E.; Fardpour, M.; Khan, K. M. Eur. J. Org. Chem. 2017, 2017, 2661.
	(d) Chen, R. Z.; Yu, J. T.; Cheng, J. Org. Biomol. Chem. 2018, 16, 1823. doi: 10.1039/C8OB00392K
[12]	(a) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. doi: 10.1021/acs.chemrev.6b00057 pmid: 31294566
	(b) Nuhant, P.; Oderinde, M. S.; Genovino, J.; Juneau, A.; Gagne, Y.; Allais, C.; Chinigo, G. M.; Choi, C.; Sach, N. W.; Bernier, L.; Fobian, Y. M.; Bundesmann, M. W.; Khunte, B.; Frenette, M.; Fadeyi, O. O. Angew. Chem., Int. Ed. 2017, 56, 15309. doi: 10.1002/anie.201707958 pmid: 31294566
	(c) Marzo, L.; Pagire, S. K.; Reiser, O.; König, B. Angew. Chem., Int. Ed. 2018, 57, 10034. doi: 10.1002/anie.201709766 pmid: 31294566
	(d) Chen, B.; Wu, L. Z.; Tung, C. H. Acc. Chem. Res. 2018, 51, 2512. doi: 10.1021/acs.accounts.8b00267 pmid: 31294566
	(e) Rostoll-Berenguer, J.; Blay, G.; Muñoz, M. C.; Pedro, J. R.; Vila, C. Org. Lett. 2019, 21, 6011. doi: 10.1021/acs.orglett.9b02157 pmid: 31294566
	(f) Xie, L. Y.; Bai, Y. S.; Xu, X. Q.; Peng, X.; Tang, H. S.; Huang, Y.; Lin, Y. W.; Cao, Z.; He, W. M. Green Chem. 2020, 22, 1720. doi: 10.1039/C9GC03899J pmid: 31294566
	(g) He, W. B.; Gao, L. Q.; Chen, X. J.; Wu, Z. L.; Huang, Y.; Cao, Z.; Xu, X. H.; He, W. M. Chin. Chem. Lett. 2020, 31, 1895. doi: 10.1016/j.cclet.2020.02.011 pmid: 31294566
	(h) Meng, N.; Lv, Y. F.; Liu, Q. S.; Liu, R. S.; Zhao, X. H.; Wei, W. Chin. Chem. Lett. 2021, 32, 258. doi: 10.1016/j.cclet.2020.11.034 pmid: 31294566
	(i) Xie, L. Y.; Peng, S.; Yang, L. H.; Peng, C.; Lin, Y. W.; Yu, X. Y.; Cao, Z.; Peng, Y. Y.; He, W. M. Green Chem. 2021, 23, 374. doi: 10.1039/D0GC02844D pmid: 31294566
	(j) Yuan, J.; Liu, Y.; Ge, Y.; Dong, S.; Song, S.; Yang, L.; Xiao, Y.; Zhang, S.; Qu, L. Chin. J. Org. Chem. 2021, 41, 4738. (in Chinese) doi: 10.6023/cjoc202110010 pmid: 31294566
	(袁金伟, 刘燕, 葛元元, 董少轩, 宋赛依, 杨亮茹, 肖咏梅, 张守仁, 屈凌波, 有机化学, 2021, 41, 4738.) doi: 10.6023/cjoc202110010 pmid: 31294566
	(k) Xiao, Y.; Yang, Y.; Zhang, F.; Feng, Y.; Cui, X. Chin. J. Org. Chem. 2021, 41, 4808. (in Chinese) doi: 10.6023/cjoc202107021 pmid: 31294566
	(肖玉娟, 杨阳, 张凡, 冯亚栋, 崔秀灵, 有机化学, 2021, 41, 4808.) doi: 10.6023/cjoc202107021 pmid: 31294566
[13]	Huff, C. A.; Cohen, R. D.; Dykstra, K. D.; Streckfuss, E.; DiRocco, D. A.; Krska, S. W. J. Org. Chem. 2016, 81, 6980. doi: 10.1021/acs.joc.6b00811
[14]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
	(b) Hurtley, A. E.; Lu, Z.; Yoon, T. P. Angew. Chem., Int. Ed. 2014, 53, 8991. doi: 10.1002/anie.201405359
	(c) Beatty, J. W.; Stephenson, C. R. J. Acc. Chem. Res. 2015, 48, 1474. doi: 10.1021/acs.accounts.5b00068
	(d) Ventre, S.; Petronijevic, F. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2015, 137, 5654. doi: 10.1021/jacs.5b02244
[15]	(a) Devari, S.; Shah, B. A. Chem. Commun. 2016, 52, 1490. doi: 10.1039/C5CC08817H
	(b) Kong, Y. L.; Xu, W. X.; Liu, X. H.; Weng, J. Q. Chin. Chem. Lett. 2020, 31, 3245. doi: 10.1016/j.cclet.2020.05.022
[16]	(a) Zhao, Y. T.; Huang, B. B.; Yang, C.; Li, B.; Gou, B. Q.; Xia, W. J. ACS Catal. 2017, 7, 2446. doi: 10.1021/acscatal.7b00192
	(b) Samanta, S.; Ravi, C.; Rao, S. N.; Joshi, A.; Adimurthy, S. Org. Biomol. Chem. 2017, 15, 9590. doi: 10.1039/C7OB02504A
	(c) Zhao, H.; Li, Z. L.; Jin, J. New J. Chem. 2019, 43, 12533. doi: 10.1039/C9NJ03106E
[17]	(a) Gandhamsetty, N.; Joung, S.; Park, S. W.; Park, S.; Chang, S. J. Am. Chem. Soc. 2014, 136, 16780. doi: 10.1021/ja510674u pmid: 25412033
	(b) Cao, Y.; Zhang, S. Q.; Antilla, J. C. ACS Catal. 2020, 10, 10914. doi: 10.1021/acscatal.0c02563 pmid: 25412033
	(c) Shu, X. M.; Jin, R. H.; Zhao, Z. R.; Cheng, T. Y.; Liu, G. H. Chem. Commun. 2018, 54, 13244. doi: 10.1039/C8CC07841F pmid: 25412033

Entry	Oxidant	Light source	Solvent	Yield^b/%
1	DTBP	Purple LEDs	H₂O	32
2	TBHP	Purple LEDs	H₂O	Trace
3	H₂O₂	Purple LEDs	H₂O	12
4	DDQ	Purple LEDs	H₂O	Trace
5	TBPB	Purple LEDs	H₂O	53
6	K₂S₂O₈	Purple LEDs	H₂O	43
7	(NH₄)₂S₂O₈	Purple LEDs	H₂O	85
8^c	(NH₄)₂S₂O₈	Purple LEDs	H₂O	61
9^d	(NH₄)₂S₂O₈	Purple LEDs	H₂O	38
10	—	Purple LEDs	H₂O	nr
11	(NH₄)₂S₂O₈	Purple LEDs	DMSO	62
12	(NH₄)₂S₂O₈	Purple LEDs	CH₃CN	46
13	(NH₄)₂S₂O₈	Purple LEDs	—	36
14	(NH₄)₂S₂O₈	White LEDs	H₂O	48
15	(NH₄)₂S₂O₈	Blue LEDs	H₂O	72
16	(NH₄)₂S₂O₈	Green LEDs	H₂O	28
17^e	(NH₄)₂S₂O₈	Sunlight	H₂O	34
18	(NH₄)₂S₂O₈	Darkness	H₂O	nr
19^f	(NH₄)₂S₂O₈	Purple LEDs	H₂O	54
20^g	(NH₄)₂S₂O₈	Purple LEDs	H₂O	51
21^h	(NH₄)₂S₂O₈	Purple LEDs	H₂O	93

Entry	Oxidant	Light source	Solvent	Yield^b/%
1	DTBP	Purple LEDs	H₂O	32
2	TBHP	Purple LEDs	H₂O	Trace
3	H₂O₂	Purple LEDs	H₂O	12
4	DDQ	Purple LEDs	H₂O	Trace
5	TBPB	Purple LEDs	H₂O	53
6	K₂S₂O₈	Purple LEDs	H₂O	43
7	(NH₄)₂S₂O₈	Purple LEDs	H₂O	85
8^c	(NH₄)₂S₂O₈	Purple LEDs	H₂O	61
9^d	(NH₄)₂S₂O₈	Purple LEDs	H₂O	38
10	—	Purple LEDs	H₂O	nr
11	(NH₄)₂S₂O₈	Purple LEDs	DMSO	62
12	(NH₄)₂S₂O₈	Purple LEDs	CH₃CN	46
13	(NH₄)₂S₂O₈	Purple LEDs	—	36
14	(NH₄)₂S₂O₈	White LEDs	H₂O	48
15	(NH₄)₂S₂O₈	Blue LEDs	H₂O	72
16	(NH₄)₂S₂O₈	Green LEDs	H₂O	28
17^e	(NH₄)₂S₂O₈	Sunlight	H₂O	34
18	(NH₄)₂S₂O₈	Darkness	H₂O	nr
19^f	(NH₄)₂S₂O₈	Purple LEDs	H₂O	54
20^g	(NH₄)₂S₂O₈	Purple LEDs	H₂O	51
21^h	(NH₄)₂S₂O₈	Purple LEDs	H₂O	93

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