无金属条件下可见光催化与溴盐协同促进烯烃的氢硅化反应研究

doi:10.6023/cjoc202210028

有机化学 ›› 2023, Vol. 43 ›› Issue (8): 2837-2847.DOI: 10.6023/cjoc202210028 上一篇下一篇

研究论文

无金属条件下可见光催化与溴盐协同促进烯烃的氢硅化反应研究

赵瑜^a^,^*,†(), 张凯^b,†, 白育斌^a, 张琰图^a, 史时辉^a^,^*()

a 延安大学化学与化工学院陕西化学反应工程重点实验室陕西延安 716000
b 江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2022-10-24 修回日期:2023-03-01 发布日期:2023-04-21
作者简介:
†共同第一作者
基金资助:
国家自然科学基金(22161047); 国家自然科学基金(22101102); 陕西省自然科学基础研究计划(2021JQ-609); 陕西省科技计划(2019JM-516); 延安大学博士科研启动基金(YDBK2018-30)

A Metal-Free Photocatalytic Hydrosilylation of Alkenes Using Bromide Salt as a Hydrogen Atom Transfer Reagent

Yu Zhao^a,*,†(), Kai Zhang^b,†, Yubin Bai^a, Yantu Zhang^a, Shihui Shi^a,*()

a College of Chemistry and Chemical Engineering, Shaanxi Key Laboratory of Chemical Reaction Engineering, Yan'an University, Yan'an, Shaanxi 716000
b School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2022-10-24 Revised:2023-03-01 Published:2023-04-21
Contact: *E-mail: zhaoyyau@163.com; shihui.shi@yau.edu.cn
About author:
†These authors contributed equally to this work
Supported by:
The National Natural Science Foundation of China(22161047); The National Natural Science Foundation of China(22101102); The Natural Science Basic Research Program of Shaanxi Province(2021JQ-609); The Science and Technology Department of Shaanxi Province(2019JM-516); The PhD Research Startup Foundation of Yan'an University(YDBK2018-30)

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摘要/Abstract

开发了一种无金属条件下可见光促进的通过选择性硅-氢键活化实现的烯烃的氢硅化反应. 该反应使用催化量的、便宜易得的溴盐作为氢原子转移试剂. 该策略展现了非常好的官能团兼容性和广泛的底物范围, 并在温和、氧化还原中性的条件下, 以中等到优秀的收率合成了有机硅化合物. 同时, 该策略也能成功地将硅基引入到生物活性分子中.

关键词: 光催化, 氢原子转移催化, 硅基自由基, 有机硅化合物

A metal-free photocatalytic hydrosilylation of alkenes through the selective activation of Si—H bond has been developed utilizing the readily available and cheaper bromide salt as the catalytic hydrogen atom transfer (HAT) reagent. This protocol features excellent functional group tolerance and broad substrate scope, affording the organosilicon compounds in moderate to excellent yields under a mild and redox-neutral process. This strategy was successfully applied for the introduction of the silyl group into bio-relevant active molecules.

Key words: photocatalysis, hydrogen atom transfer catalysis, silyl radical, organosilicon compound

引用此文

赵瑜, 张凯, 白育斌, 张琰图, 史时辉. 无金属条件下可见光催化与溴盐协同促进烯烃的氢硅化反应研究[J]. 有机化学, 2023, 43(8): 2837-2847.

Yu Zhao, Kai Zhang, Yubin Bai, Yantu Zhang, Shihui Shi. A Metal-Free Photocatalytic Hydrosilylation of Alkenes Using Bromide Salt as a Hydrogen Atom Transfer Reagent[J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2837-2847.

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图/表 7

Figure 1. Examples of biologically active silicon-containing compounds

Scheme 1. Photocatalytic silylation reactions

Entry	Photocat.	x	Solvent	Yield^b/%
1	4CzIPN	15	MeCN	97 (95)
2	Eosin Y	15	MeCN	92
3	Rhodamin	15	MeCN	96
4	4C_ZIPN (3 mol%)	15	MeCN	98
5	4C_ZIPN (3 mol%)	5	MeCN	98 (94)
6	4C_ZIPN (3 mol%)	5	THF	81
7	4C_ZIPN (3 mol%)	5	DCM	91
8^c	4C_ZIPN (3 mol%)	5	MeCN	64
9^d	No	5	MeCN	0
10^e	4C_ZIPN (3 mol%)	5	MeCN	0
11^f	4C_ZIPN (3 mol%)	5	MeCN	59

Table 1. Reaction optimizationa

Scheme 2. Photocatalytic hydrosilylation irradiated by sunlight

Scheme 3. Mechanistic studies

Figure 2. Fluorescence quenching experiments and Stern-Volmer liner

Scheme 4. Proposed mechanism

参考文献 16

[1]	Application of the organosilicons: (a) Lee, K. L. Angew. Chem., Int. Ed. 2017, 56, 3665. doi: 10.1002/anie.v56.13 pmid: 29039662
	(b) Franz, A. K.; Wilson, S. O. J. Med. Chem. 2013, 56, 388. doi: 10.1021/jm3010114 pmid: 29039662
	(c) Hardman-Baldwin, A. M.; Mattson, A. E. ChemSusChem 2014, 7, 3275. doi: 10.1002/cssc.201402783 pmid: 29039662
	(d) Wieting, M.; Fisher, T. J.; Schafer, A. G.; Visco, M. D. Eur. J. Org. Chem. 2015, 2015, 525. doi: 10.1002/ejoc.201403441 pmid: 29039662
	(e) Ramesh, R.; Reddy, D. S. J. Med. Chem. 2018, 61, 3779. doi: 10.1021/acs.jmedchem.7b00718 pmid: 29039662
	(f) Hu, J.; Zhang, A. X.; Chen, L.; Li, W. Q.; Zeng, X. H. Silicone Mater. 2019, 33, 218. pmid: 29039662
[2]	(a) Remond, E.; Martin, C.; Martinez, J.; Cavelier, F. Chem. Rev. 2016, 116, 11654. doi: 10.1021/acs.chemrev.6b00122
	(b) Komiyama, T.; Minami, Y.; Hiyama, T. ACS Catal. 2016, 7, 631. doi: 10.1021/acscatal.6b02374
	(c) de Almeida, L. D.; Wang, H.; Junge, K.; Cui, X.; Beller, M. Angew. Chem., Int. Ed. 2021, 60, 550. doi: 10.1002/anie.v60.2
[3]	Reviews for the advances of silyl radical: (a) Zhang, X.; Fang, J.; Cai, C.; Lu, G. Chin. Chem. Lett. 2021, 32, 1280. doi: 10.1016/j.cclet.2020.09.058
	(b) Shang, X.; Liu, Z. Q. Org. Biomol. Chem. 2016, 14, 7829. doi: 10.1039/C6OB00797J
	(c) Li, J. S.; Wu, J. ChemPhotoChem 2018, 2, 839. doi: 10.1002/cptc.v2.10
	(d) Huang, H. T.; Li, T.; Wang, J. Z.; Qin, G. P.; Xiao, T. B. Chin. J. Org. Chem. 2019, 39, 1511. (in Chinese)
	( 黄鸿泰, 李涛, 王家状, 秦贵平, 肖铁波, 有机化学, 2019, 39, 1511.) doi: 10.6023/cjoc201903078
	(e) Wilkinson, J. R.; Nuyen, C. E.; Carpenter, T. S.; Harruff, S. R.; Van Hoveln, R. ACS Catal. 2019, 9, 8961. doi: 10.1021/acscatal.9b02762
[4]	(a) Sakamoto, R.; Nguyen, B.-N.; Maruoka, K. Asian J. Org. Chem. 2018, 7, 1085. doi: 10.1002/ajoc.v7.6 pmid: 30475364
	(b) Chang, X. H.; Wang, Z. L.; Zhao, M.; Yang, C.; Li, J. J.; Ma, W. W.; Xu, Y. H. Org. Lett. 2020, 22, 1326. doi: 10.1021/acs.orglett.9b04645 pmid: 30475364
	(c) Zhang, C.; Pi, J.; Wang, L.; Liu, P.; Sun, P. Org. Biomol. Chem. 2018, 16, 9223. doi: 10.1039/c8ob02670j pmid: 30475364
	(d) Lin, Y. M.; Lu, G. P.; Wang, R. K.; Yi, W. B. Org. Lett. 2017, 19, 1100. doi: 10.1021/acs.orglett.7b00126 pmid: 30475364
	(e) Yang, Y.; Song, R. J.; Ouyang, X. H.; Wang, C. Y.; Li, J. H.; Luo, S. Angew. Chem., Int. Ed. 2017, 56, 7916. doi: 10.1002/anie.201702349 pmid: 30475364
	(f) Gu, J.; Cai, C. Chem. Commun. 2016, 52, 10779. doi: 10.1039/C6CC05509E pmid: 30475364
	(g) Zhang, X.; Liu, M.-X.; Wang, T.-L.; Wang, Y.-Q.; Wang, X.-C.; Quan, Z.-J. Org. Chem. Front. 2019, 6, 3365. doi: 10.1039/c9qo00819e pmid: 30475364
[5]	Liu, W. B.; Schuman, D. P.; Yang, Y. F.; Toutov, A. A.; Liang, Y.; Klare, H. F. T.; Nesnas, N.; Oestreich, M.; Blackmond, D. G.; Virgil, S. C.; Banerjee, S.; Zare, R. N.; Grubbs, R. H.; Houk, K. N.; Stoltz, B. M. J. Am. Chem. Soc. 2017, 139, 6867. doi: 10.1021/jacs.6b13031
[6]	Reviews for photocatalytic reactions: (a) Lu, F.-D.; Chen, J.; Jiang, X.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2021, 50, 12808. doi: 10.1039/D1CS00210D
	(b) Zhang, M.-M.; Qu, B.-L.; Shi, B.; Xiao, W.-J.; Lu, L.-Q. Chem. Soc. Rev. 2022, 51, 4146. doi: 10.1039/D1CS00897H
	(c) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030
	(d) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
	(e) Shaw, M. H.; Twilton, J.; MacMillan, D. W. C. J. Org. Chem. 2016, 81, 6898. doi: 10.1021/acs.joc.6b01449
	(f) Qiao, B.; Jiang, Z. ChemPhotoChem 2018, 2, 703. doi: 10.1002/cptc.v2.8
	(g) Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075. doi: 10.1021/acs.chemrev.6b00057
[7]	(a) Yang, C.; Wang, J.; Li, J.; Ma, W.; An, K.; He, W.; Jiang, C. Adv. Synth. Catal. 2018, 360, 3049. doi: 10.1002/adsc.201800417
	(b) Zhang, X.-Y.; Wu, X.-Y.; Zhang, B.; Wei, Y.; Shi, M. ACS Catal. 2021, 11, 4372. doi: 10.1021/acscatal.1c00240
[8]	Xu, N. X.; Li, B. X.; Wang, C.; Uchiyama, M. Angew. Chem., Int. Ed. 2020, 59, 10639. doi: 10.1002/anie.v59.26
[9]	(a) Yu, X.; Lubbesmeyer, M.; Studer, A. Angew. Chem. Int. Ed. 2021, 60, 675. doi: 10.1002/anie.v60.2
	(b) Yu, X.; Daniliuc, C. G.; Alasmary, F. A.; Studer, A. Angew. Chem., Int. Ed. 2021, 60, 23335. doi: 10.1002/anie.v60.43
[10]	Liu, R.; Chia, S. P. M.; Goh, Y. Y.; Cheo, H. W.; Fan, B.; Li, R.; Zhou, R.; Wu, J. Eur. J. Org. Chem. 2020, 2020, 1459. doi: 10.1002/ejoc.v2020.10
[11]	(a) Liu, S.; Pan, P.; Fan, H.; Li, H.; Wang, W.; Zhang, Y. Chem. Sci. 2019, 10, 3817. doi: 10.1039/C9SC00046A
	(b) Rammal, F.; Gao, D.; Boujnah, S.; Hussein, A. A.; Lalevée, J.; Gaumont, A.-C.; Morlet-Savary, F.; Lakhdar, S. ACS Catal. 2020, 10, 13710. doi: 10.1021/acscatal.0c03726
	(c) Fan, X.; Xiao, P.; Jiao, Z.; Yang, T.; Dai, X.; Xu, W.; Tan, J. D.; Cui, G.; Su, H.; Fang, W.; Wu, J. Angew. Chem., Int. Ed. 2019, 58, 12580. doi: 10.1002/anie.v58.36
	(d) Yu, W.-L.; Luo, Y.-C.; Yan, L.; Liu, D.; Wang, Z.-Y.; Xu, P.-F. Angew. Chem., Int. Ed. 2019, 58, 10941. doi: 10.1002/anie.v58.32
	(e) Zhou, R.; Li, J.; Cheo, H. W.; Chua, R.; Zhan, G.; Hou, Z.; Wu, J. Chem. Sci. 2019, 10, 7340. doi: 10.1039/C9SC02818H
	(f) Huang, Z.; Chen, Z.; Jiang, Y.; Li, N.; Yang, S.; Wang, G.; Pan, X. J. Am. Chem. Soc. 2021, 143, 19167. doi: 10.1021/jacs.1c09263
	(g) Yue, F.; Liu, J.; Ma, H.; Liu, Y.; Dong, J.; Wang, Q. Org. Lett. 2022, 24, 4019. doi: 10.1021/acs.orglett.2c01448
	(h) Xu, W. G.; Xia, C. J.; Shao, Q.; Zhang, Q.; Liu, M. R.; Zhang, H. W.; Wu, M. B. Org. Chem. Front. 2022, 9, 4949. doi: 10.1039/D2QO00894G
	(i) Shi, Q.; Xu, M.; Chang, R.; Ramanathan, D.; Penin, B.; Funes-Ardoiz, I.; Ye, J. Nat. Commun. 2022, 13, 4453. doi: 10.1038/s41467-022-32238-8
	(g) Zhong, M.; Pannecoucke, X.; Jubault, P.; Poisson, T. Chem.-Eur. J. 2021, 27, 11818. doi: 10.1002/chem.v27.46
	(k) Takemura, N.; Sumida, Y.; Ohmiya, H. ACS Catal. 2022, 12, 7804. doi: 10.1021/acscatal.2c01964
[12]	(a) Zhou, R.; Goh, Y. Y.; Liu, H.; Tao, H.; Li, L.; Wu, J. Angew. Chem., Int. Ed. 2017, 56, 16621. doi: 10.1002/anie.201711250
	(b) Hou, J.; Ee, A.; Cao, H.; Ong, H. W.; Xu, J. H.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 17220. doi: 10.1002/anie.v57.52
[13]	Zhang, Z.; Hu, X. ACS Catal. 2019, 10, 777. doi: 10.1021/acscatal.9b04916
[14]	(a) Zou, L.; Li, P.; Wang, B.; Wang, L. Green Chem. 2019, 21, 3362. doi: 10.1039/C9GC00938H
	(b) Xu, J.; Huang, L.; He, L.; Ni, Z.; Shen, J.; Li, X.; Chen, K.; Li, W.; Zhang, P. Green Chem. 2021, 23, 2123. doi: 10.1039/D0GC04235H
[15]	Luo, J.; Zhang, J. ACS Catal. 2016, 6, 873. doi: 10.1021/acscatal.5b02204
[16]	Zhang, P.; Le, C. C.; MacMillan, D. W. J. Am. Chem. Soc. 2016, 138, 8084. doi: 10.1021/jacs.6b04818

无金属条件下可见光催化与溴盐协同促进烯烃的氢硅化反应研究

A Metal-Free Photocatalytic Hydrosilylation of Alkenes Using Bromide Salt as a Hydrogen Atom Transfer Reagent

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