邻二碘芳烃和氢化钠产生芳炔用于硫醇的邻碘芳基化反应

doi:10.6023/cjoc202312022

摘要/Abstract

该方法使用廉价易得的试剂邻二碘芳烃和氢化钠生成苯炔, 然后与硫醇发生反应, 简单高效地合成邻碘芳基硫醚. 值得注意的是, 在反应中没有观察到像过渡金属催化那样得到的二硫醚副产物. 该方法操作简单, 条件温和, 底物范围广泛, 很多情况下都给出较高收率的产物.

关键词: 芳炔, 硫醇, 邻二碘芳烃, 氢化钠, 邻碘芳基硫醚

A simple and efficient method is described for the synthesis of o-iodoaryl thioethers by the reaction of thiols and aryne. The aryne is generated from inexpensive and readily available reagents o-diiodoarene and sodium hydride. Remarkably, no disulfide substituted byproduct was observed in the reactions which is different from transition metal-catalyzed process. This method features simple operation, mild reaction conditions, broad substrate scope, and high reaction yields for many cases.

Key words: aryne, thiol, o-diiodoarene, sodium hydride, o-iodoaryl thioether

引用此文

刘典范, 王健智, 王梦晴, 陈晓蓓, 胡延维, 张士磊. 邻二碘芳烃和氢化钠产生芳炔用于硫醇的邻碘芳基化反应[J]. 有机化学, 2024, 44(7): 2363-2370.

Dianfan Liu, Jianzhi Wang, Mengqing Wang, Xiaobei Chen, Yanwei Hu, Shilei Zhang. o-Iodoarylation of Thiols Enabled by Aryne Generated from o-Diiodoarene and Sodium Hydride[J]. Chinese Journal of Organic Chemistry, 2024, 44(7): 2363-2370.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

图/表 6

参考文献 66

[1]	Wang, N.; Saidhareddya, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246.
[2]	Liu, H.; Jiang, X. Chem. Asian J. 2013, 8, 2546.
[3]	Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521. doi: 10.1021/acs.chemrev.6b00697 pmid: 28418240
[4]	Criscieli, B.; Beatriz, S.; Caren, S.; George, B.; Beatriz, S.; Nelson, C. Curr. Org. Synth. 2020, 17, 192. doi: 10.2174/1570179417666200212113412 pmid: 32091342
[5]	Wu, Q.; Bell, B. A.; Yan, J. X.; Chevrette, M. G.; Brittin, N. J.; Zhu, Y.; Chanana, S.; Maity, M.; Braun, D. R.; Wheaton, A. M.; Guzei, I. A.; Ge, Y.; Rajski, S. R.; Thomas, M. G.; Bugni, T. S. J. Am. Chem. Soc. 2023, 145, 58.
[6]	Cinar, M. E.; Ozturk, T. Chem. Rev. 2015, 115, 3036.
[7]	Zhang, M.; Zhang, B. B.; Lin, Q.; Jiang, Z.; Zhang, J.; Li, Y.; Pei, S.; Han, X.; Xiong, H.; Liang, X.; Lin, Y.; Wei, Z.; Zhang, F.; Zhang, X.; Wang, Z.-X.; Shi, Q.; Huang, H. Angew. Chem., Int. Ed. 2023, 62, e202306307.
[8]	Lou, J.; Wang, Q.; Wu, P.; Wang, H.; Zhou, Y.-G.; Yu, Z. Chem. Soc. Rev. 2020, 49, 4307.
[9]	Lin, Y.; Li, Z.; Ma, H.; Wang, Y.; Wang, X.; Song, S.; Zhao, L.; Wu, S.; Tian, S.; Fu, C.; Luo, L.; Zhu, F.; He, S.; Zheng, J.; Zhang, X. Chem. Med. Chem. 2020, 15, 1150.
[10]	Ji, X.; Li, Z. Med. Res. Rev. 2020, 40, 1519.
[11]	Huang, X.-L.; Chen, J.-L.; Li, X.-L.; Zhao, L.; Cui, Y.-D.; Liu, J.-Y.; Morris-Natschke, S. L.; Masuo, G.; Cheng, Y.-Y.; Lee, K.-H.; Chen, D.-F.; Zhang, J. J. Asian Nat. Prod. Res. 2021, 23, 703.
[12]	Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2022, 122, 16110. doi: 10.1021/acs.chemrev.1c00836 pmid: 36112510
[13]	Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596. doi: 10.1021/cr100347k pmid: 21391564
[14]	Ghaderi, A. Tetrahedron 2016, 72, 4758.
[15]	Sundaravelu, N.; Sangeetha, S.; Sekar, G. Org. Biomol. Chem. 2021, 19, 1459. doi: 10.1039/d0ob02320e pmid: 33528480
[16]	Kanchana, U. S.; Diana, E. J.; Mathew, T. V. Asian J. Org. Chem. 2022, 11, e202200038.
[17]	Lee, C. F.; Liu, Y. C.; Badsara, S. S. Chem. Asian J. 2014, 9, 706.
[18]	Zhao, S.; Chen, K.; Zhang, L.; Yang, W.; Huang, D. Adv. Synth. Catal. 2020, 362, 3516.
[19]	Bag, R.; Sharma, N. K. Org. Chem. Front. 2023, 10, 1252.
[20]	Chaitanya, M.; Anbarasan, P. Org. Lett. 2018, 20, 3362. doi: 10.1021/acs.orglett.8b01281 pmid: 29775070
[21]	Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.-X.; Wu, L.-Z.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273.
[22]	Li, M.; Wang, J. J. Org. Lett. 2018, 20, 6490.
[23]	Kang, Y.-S.; Zhang, P.; Li, M.-Y.; Chen, Y.-K.; Xu, H.-J.; Zhao, J.; Sun, W.-Y.; Yu, J.-Q.; Lu, Y. Angew. Chem., Int. Ed. 2019, 58, 9099.
[24]	Fernandes, R. A.; Bhowmik, A.; Yadav, S. S. Org. Biomol. Chem. 2020, 18, 9583. doi: 10.1039/d0ob02035d pmid: 33206103
[25]	Sun, N.; Zheng, K.; Zhang, M.; Zheng, G.; Jin, L.; Hu, B.; Shen, Z.; Hu, X. Green Chem. 2023, 25, 2782.
[26]	Song, C.; Liu, K.; Dong, X.; Chiang, C.-W.; Lei, A. Synlett 2019, 30,1149.
[27]	Yang, D.; Yan, Q.; Zhu, E.; Lv, J.; He, W. M. Chin. Chem. Lett. 2022, 33, 1798.
[28]	Annamalai, P.; Liu, K.-C.; Badsara, S. S.; Lee, C.-F. Chem. Rec. 2021, 21, 3674.
[29]	Cabrera‐Afonso, M. J.; Granados, A.; Molander, G. A. Angew. Chem., Int. Ed. 2022, 61, e202202706.
[30]	Zhang, M.; Wang, B.; Cao, Y.; Liu, Y.; Wang, Z.; Wang, Q. Org. Lett. 2022, 24, 8895.
[31]	Pramanik, M.; Choudhuri, K.; Mal, P. Org. Biomol. Chem. 2020, 18, 8771. doi: 10.1039/d0ob01741h pmid: 33073827
[32]	Saroha, M.; Sindhu, J.; Kumar, S.; Bhasin, K. K.; Khurana, J. M.; Varma, R. S.; Tomar, D. ChemistrySelect 2021, 6, 13077.
[33]	Chen, S.; Wen, Q.; Zhu, Y.; Ji, Y.; Pu, Y.; Liu, Z.; He, Y.; Feng, Z. Chin. Chem. Lett. 2022, 33, 5101.
[34]	Yang, P.; Zheng, C.; Nie, Y. H.; You, S. L. Chem. Sci. 2020, 11, 6830.
[35]	Zhu, X.; Li, W.; Luo, X.; Deng, G.; Liang, Y.; Liu, J. Green Chem. 2018, 20, 1970.
[36]	Li, X.; Zhou, B.; Yang, R.-Z.; Yang, F.-M.; Liang, R.-X.; Liu, R.-R.; Jia, Y.-X. J. Am. Chem. Soc. 2018, 140, 13945.
[37]	Flynn, A. R.; McDaniel, K.; Hughes, M.; Vogt, D.; Jui, N. T. J. Am. Chem. Soc. 2020, 142, 9163.
[38]	Zhou, B.; Wang, H.; Cao, Z.-Y.; Zhu, J.-W.; Liang, R.-X.; Hong, X.; Jia, Y.-X. Nat. Commun. 2020, 11, 4380. doi: 10.1038/s41467-020-18137-w pmid: 32873772
[39]	Liu, W.; Min, H.; Zhu, X.; Deng, G.; Liang, Y. Org. Biomol. Chem. 2017, 15, 9804.
[40]	Li, L.; Liu, X.-L.; Qi, Z.; Yang, A.-H.; Ma, A.-J.; Peng, J.-B. Org. Lett. 2022, 24, 1201.
[41]	Ca, N. D.; Fontana, M.; Motti, E.; Catellani, M. Chem. Res. 2016, 49, 1389.
[42]	Wang, J.; Dong, G. Chem. Rev. 2019, 119, 7478.
[43]	Liu, J.; Lin, H.; Jiang, H.; Huang, L. Org. Lett. 2022, 24, 484.
[44]	Zeng, Y.; Li, G.; Hu, J. Angew. Chem., Int. Ed. 2015, 54, 10773.
[45]	Zeng, Y.; Zhang, L.; Zhao, Y.; Ni, C.; Zhao, J.; Hu, J. J. Am. Chem. Soc. 2013, 135, 2955.
[46]	Cao, W.; Niu, S. L.; Shuai, L.; Xiao, Q. Chem. Commun. 2020, 56, 972.
[47]	Wang, W.; Ding, M.; Zhao, C. G.; Chen, S.; Zhu, C.; Han, J.; Li, W.; Xie, J. Angew. Chem., Int. Ed. 2023, 62, e202304019.
[48]	Cao, W. X.; Zhu, L.; He, Y.; Wang, R.; Liu, M.; Ouyang, Q.; Xiao, Q. Angew. Chem., Int. Ed. 2023, e202305146.
[49]	Chen, D.; Yang, C.; Li, M.; Zhao, G.; Wang, W.; Wang, X.; Quan, Z. Chin. J. Org. Chem. 2023, 43, 503. (in Chinese)
	(陈东平, 杨春红, 李明, 赵国孝, 王文鹏, 王喜存, 权正军, 有机化学, 2023, 43, 503.)
[50]	Yan, Q.; Fan, R.; Liu, B.; Su, S.; Wang, B.; Yao, T.; Tan, J. Chin. J. Org. Chem. 2021, 41, 455. (in Chinese)
	(闫强, 范荣, 刘斌斌, 苏帅松, 王勃, 姚团利, 谭嘉靖, 有机化学, 2021, 41, 455.)
[51]	Liu, Y.; Wang, H.; Cao, X.; Fang, Z.; Wan, J. P. Synthesis 2013, 45, 2977.
[52]	Carril, M.; SanMartin, R.; Domínguez, E.; Tellitu, I. Chem.-Eur. J. 2007, 13, 5100.
[53]	Reinhard, D. L.; Heinen, F.; Stoesser, J.; Engelage, E.; Huber, S. M. Helv. Chim. Acta 2021, 104, e2000221.
[54]	Luo, F.; Li, C.; Ji, P.; Zhou, Y.; Gui, J.; Chen, L.; Yin, Y.; Zhang, X; Hu, Y.; Chen, X.; Liu, X.; Chen, X.; Yu, Z.; Wang, W.; Zhang, S. Chem 2023, 9, 2620.
[55]	Jiang, Y.; Zhu, W.; Huang, J.; Luo, F.; Chen, X.; Fang, C.; Chen, X.; Liu, S.; Hu, Y.; Zhang, S. Org. Chem. Front. 2024, 11, 12.
[56]	Hu, M.; Liu, D.; Liu, Y.; Luo, F.; Chen, X.; Yin, Y.; Zhang, S.; Hu, Y. Adv. Synth. Catal. 2024, 366, 1538.
[57]	Liu, Y.; Mao, Y.; Hu, Y.; Gui, J.; Wang, L.; Wang, W.; Zhang, S. Adv. Synth. Catal. 2019, 361, 1554. doi: 10.1002/adsc.201801676
[58]	Sun, W.; Chen, X.; Hu, Y.; Geng, H.; Jiang, Y.; Zhou, Y.; Zhu, W.; Hu, M.; Hu, H.; Wang, X.; Wang, X.; Zhang, S.; Hu, Y. Tetrahedron Lett. 2020, 61, 152442.
[59]	Gui, J.; Cai, X.; Chen, L.; Zhou, Y.; Zhu, W.; Jiang, Y.; Hu, M.; Chen, X.; Hu, Y.; Zhang, S. Org. Chem. Front. 2021, 8, 4685.
[60]	Luo, F.; Chen, X.; Yu, J.; Yin, Y.; Hu, X.; Hu, Y.; Liu, X.; Chen, X.; Zhang, S.; Hu, Y. Synthesis 2023, 55, 1451.
[61]	Mao, Y.; Liu, Y.; Hu, Y.; Wang, L.; Zhang, S.; Wang, W. ACS Catal. 2018, 8, 3016.
[62]	Leroux, F.; Schlosser, M. Angew. Chem., Int. Ed. 2002, 41, 4272.
[63]	Leroux, F. R.; Bonnafoux, L.; Heiss, C.; Colobert, F.; Lanfranchi, D. A. Adv. Synth. Catal. 2007, 349, 2705.
[64]	Bonnafoux, L.; Colobert, F.; Leroux, F. R. Synlett 2010, 2953.
[65]	Diemer, V.; Begaud, M.; Leroux, F. R.; Colobert, F. Eur. J. Org. Chem. 2011, 341.
[66]	Berthelot-Brehier, A.; Panossian, A.; Colobert, F.; Leroux, F. R. Org. Chem. Front. 2015, 2, 634.

Entry	Base (equiv.)	Solvent	T/℃	Yield^b/%
1	NaH (3.0)	THF	rt	52
2	NaH (3.0)	THF	35	56
3	NaH (3.0)	THF	40	71
4	NaH (3.0)	THF	50	65
5	NaH (3.0)	THF	60	42
6	NaH (5.0)	THF	40	68
7^c	NaH (3.0)	THF	40	56
8	NaH (3.0)	DMA	40	63
9	NaH (3.0)	CH₃CN	40	12
10	NaH (3.0)	Dioxane	40	nr^d
11	NaH (3.0)	DMF	40	36
12	KH (3.0)	THF	40	nr
13	CaH₂ (2.0)	THF	40	24
14	LiH (3.0)	THF	40	nr
15	BuLi (2.5)	THF	-78	35
16^e	NaH (3.0)	THF	40	36
17	K₂CO₃ (2.0)	DMA	40	nr
18	NaOH (3.0)	DMA	40	nr

Entry	Base (equiv.)	Solvent	T/℃	Yield^b/%
1	NaH (3.0)	THF	rt	52
2	NaH (3.0)	THF	35	56
3	NaH (3.0)	THF	40	71
4	NaH (3.0)	THF	50	65
5	NaH (3.0)	THF	60	42
6	NaH (5.0)	THF	40	68
7^c	NaH (3.0)	THF	40	56
8	NaH (3.0)	DMA	40	63
9	NaH (3.0)	CH₃CN	40	12
10	NaH (3.0)	Dioxane	40	nr^d
11	NaH (3.0)	DMF	40	36
12	KH (3.0)	THF	40	nr
13	CaH₂ (2.0)	THF	40	24
14	LiH (3.0)	THF	40	nr
15	BuLi (2.5)	THF	-78	35
16^e	NaH (3.0)	THF	40	36
17	K₂CO₃ (2.0)	DMA	40	nr
18	NaOH (3.0)	DMA	40	nr