Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes

doi:10.6023/cjoc202106014

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (12): 4815-4824.DOI: 10.6023/cjoc202106014 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑；绿色合成化学专辑；热点论文虚拟合集

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可见光催化的1,6-烯炔参与的Kharasch加成反应

耿芳洲^a^,^b, 王世超^a, 宋克贤^a, 郝文娟^a^,^b^,^*(), 姜波^a^,^b^,^*()

a 江苏师范大学化学与材料科学学院江苏徐州 221116
b 江苏师范大学敬文书院江苏徐州 221116

收稿日期:2021-06-07 修回日期:2021-07-14 发布日期:2021-07-19
通讯作者: 郝文娟, 姜波
作者简介:
† 共同第一作者
基金资助:
国家自然科学基金(21971090); 江苏省品牌专业基金和国家级大学生创新创业训练计划(202010320060Z)

Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes

Fangzhou Geng^a^,^b, Shichao Wang^a, Kexian Song^a, Wenjuan Hao^a^,^b(), Bo Jiang^a^,^b()

a School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, Jiangsu 221116
b C.W. Chu College, Jiangsu Normal University, Xuzhou, Jiangsu 221116

Received:2021-06-07 Revised:2021-07-14 Published:2021-07-19
Contact: Wenjuan Hao, Bo Jiang
About author:
† These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21971090); Top-notch Academic Programs Project of Jiangsu Higher Education Institutions and National College Studentʼs Innovation and Entrepreneurship Training Program(202010320060Z)

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Abstract

A new visible-light-driven photocatalytic Kharasch-type addition of 1,6-enynes was reported. By using the characteristics of the in-situ-generation of trihalomethyl radicals from photocatalytic reduction of trichloromethane bromide and carbon tetrabromide, fac-Ir(ppy)₃-catalyzed Kharasch-type addition of 1,6-enynes of these polyhalogenated hydrocarbon substrates at room temperature was conducted under visible-light irradiation, regioselectively affording 1-indanone derivatives with an exocyclic double bond and a quaternary carbon in moderate to good yields. Based on the experimental results and literature reports, a reasonable reaction mechanism was proposed, which involved the in-situ-generation of trihalomethyl radicals, radical-induced addition-cyclization and radical cross coupling. In addition, this protocol featured wide substrate scope, high functional group compatibility, 100% atomic utilization, and mild conditions as well as simple operation. It provides a green, mild, and efficient synthetic strategy for the construction of 1-indanone skeleton with potential application, which is consistent with the concept of green chemistry.

Key words: Kharasch-type addition, photocatalysis, 1,6-enynes, 1-indanones

Cite this article

Fangzhou Geng, Shichao Wang, Kexian Song, Wenjuan Hao, Bo Jiang. Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4815-4824.

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References 17

[1]	(a) Nagle, D. G.; Zhou, Y. D.; Park, P. U.; Paul, V. J.; Rajbhandari, I.; Duncan, C. J. G.; Pasco, D. S. J. Nat. Prod. 2000, 63, 1431. pmid: 7490731
	(b) Ito, T.; anaka, T.; Iinuma, T. M.; Nakaya, K.; Takahashi, Y.; Sawa, R.; Murata, J.; Darnaedi, D. J. Nat. Prod. 2004, 67, 932. doi: 10.1021/np030236r pmid: 7490731
	(c) Dai, J. R.; Hallock, Y. F.; Cardellina, J. H.; Boyd, M. R. J. Nat. Prod. 1998, 61, 351. pmid: 7490731
	(d) DeSolms, S. J.; Woltersdorf, O. W.; Cragoe, E. J.; Watson, L. S.; Fanelli, G. M. J. Med. Chem. 1978, 21, 437. doi: 10.1021/jm00203a006 pmid: 7490731
	(e) Sugimoto, H.; Iimura, Y.; Yamanishi, Y.; Yamatsu, K. J. Med. Chem. 1995, 38, 4821. pmid: 7490731
[2]	(a) Anstead, G. M.; Wilson, S. R.; Katzenellenbogen, J. A. J. Med. Chem. 1989, 32, 2163. pmid: 15876535
	(b) McDevitt, R. E.; Malamas, M. S.; Manas, E. S.; Unwalla, R. J.; Xu, Z. B.; Miller, C. P.; Harris, H. A. Bioorg. Med. Chem. Lett. 2005, 15, 3137. pmid: 15876535
	(c) Park, C. H.; Siomboing, X.; Yous, S.; Gressier, B; Luyckx, M.; Chavatte, P. Eur. J. Med. Chem. 2002, 37, 461-468. doi: 10.1016/S0223-5234(02)01373-9 pmid: 15876535
[3]	(a) Ahn, J. H.; Shin, M. S.; Jung, S. H.; Kang, S. K.; Kim, K. R.; Dal Rhee, S.; Jung, W. H.; Yang, S. D.; Kim, S. J.; Woo, J. R. J. Med. Chem. 2006, 49, 4781. doi: 10.1021/jm060389m pmid: 22536944
	(b) Kiselev, E.; DeGuire, S.; Morrell, A.; Agama, K.; Dexheimer, T. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2011, 54, 6106. doi: 10.1021/jm200719v pmid: 22536944
	(c) Nguyen, T. X.; Morrell, A.; Conda-Sheridan, M.; Marchand, C.; Agama, K.; Bermingam, A.; Stephen, A. G; Chergui, A.; Naumova, A.; Fisher, R.; O’Keefe, B. R.; Pommier, Y.; Cushman, M. J. Med. Chem. 2012, 55, 4457. doi: 10.1021/jm300335n pmid: 22536944
	(d) Gamo, F. J.; Sanz, L. M.; Vidal, J.; de, C. C.; Alvarez, E.; Lavandera, J. L.; Vanderwall, D. E. Green, D. V. S.; Kumar, V.; Hasan, S.; Brown, J. R.; Peishoff, C. E.; Cardon, L. R.; Garcia-Bustos, J. F. Nature 2010, 465, 305. doi: 10.1038/nature09107 pmid: 22536944
[4]	(a) Liu, W.; Buck, M.; Chen, N.; Shang, M.; Taylor, N. J.; Asoud, J.; Wu, X.; Hasinoff, B. B.; Dmitrienko, G. I. Org. Lett. 2007, 9, 2915. doi: 10.1021/ol0712374 pmid: 19902905
	(b) Jeffrey, J. L.; Sarpong, R.; Org. Lett. 2009, 11, 5450. doi: 10.1021/ol902141z pmid: 19902905
[5]	(a) Cappelli, A.; Pericot Mohr, G. L.; Giuliani, G.; Galeazzi, S.; Anzini, M.; Mennuni, L.; Ferrari, F.; Makovec, F.; Kleinrath, E. M.; Langer, T.; Valoti, M.; Giorgi, G.; Vomero, S. J. Med. Chem. 2006, 49, 6451. pmid: 17064065
	(b) Tseng, C. H.; Tzeng, C. C.; Yang, C. L.; Lu, P. J.; Chen, H. L.; Li, H. Y.; Chuang, Y. C.; Yang, C. N.; Chen, Y. L. J. Med. Chem. 2010, 53, 6169. pmid: 17064065
[6]	(a) Koelsch, C. F. J. Am. Chem. Soc. 1932, 54, 2487. doi: 10.1021/ja01345a046
	(b) Frank, R. L.; Eklund, H. J.; Richter, W.; Vanneman, C. R.; Wennerberg, A. N. J. Am. Chem. Soc. 1944, 66, 1. doi: 10.1021/ja01229a001
[7]	(a) Bergmann, E. D. J. Org. Chem. 1956, 21, 461. doi: 10.1021/jo01110a023
	(b) Manning, C.; McClory, M. R.; McCullough, J. J. J. Org. Chem. 1981, 46, 919. doi: 10.1021/jo00318a018
	(c) Dong, D.-Q.; Chen, W.-J.; Chen, D.-M.; Li, L. X..; Li, G. H.; Wang, Z. L.; Deng, Q.; Long, S. Chin. J. Org. Chem. 2019, 39, 3190. (in Chinese) doi: 10.6023/cjoc201904070
	( 董道青, 陈文静, 陈德茂, 李丽霞, 李光辉, 王祖利, 邓企, 龙姝, 有机化学, 2019, 39, 3190.) doi: 10.6023/cjoc201904070
[8]	(a) Chernyak, N.; Gorelsky, S. I.; Gevorgyan, V. Angew. Chem. Int. Ed. 2011, 50, 2342. doi: 10.1002/anie.201006751
	(b) Shintani, R.; Takatsu, K.; Hayashi, T. Angew. Chem. Int. Ed. 2007, 46, 3735. doi: 10.1002/(ISSN)1521-3773
	(c) He, G.; Wu, C.; Zhou, J.; Yang, Q.; Zhang, C.; Zhou, Y.; Zhang, H.; Liu, H. J. Org. Chem. 2018, 83, 13356. doi: 10.1021/acs.joc.8b02149
	(d) Song, L.; Tian, G.; Van der Eycken, E. V. Chem. Eur. J. 2019, 25, 7645. doi: 10.1002/chem.v25.32
	(e) Liu, Q.-S.; Lv, Y.-F.; Liu, R.-S.; Zhao, X.-H.; Wang, J.-W.; Wei, W. Chin. Chem. Lett. 2021, 32, 136. doi: 10.1016/j.cclet.2020.11.059
[9]	(a) Zhang, Y. L.; Sun, K.; Lv, Q. Y.; Chen, X. L.; Qu, L. B.; Yu, B. Chin. Chem. Lett. 2019, 30, 1361. doi: 10.1016/j.cclet.2019.03.034
	(b) Zhang, T.-S.; Hao, W.-J.; Wang, R.; Wang, S.-C.; Tu, S.-J.; Jiang, B. Green Chem. 2020, 22, 4259. doi: 10.1039/D0GC00771D
	(c) Shen, Z.-J.; Wu, Y.-N.; He, C.-L.; He, L.; Hao, W.-J.; Wang, A.-F.; Tu, S.-J.; Jiang, B. Chem. Commun. 2018, 54, 445. doi: 10.1039/C7CC08516H
	(d) Wu, Y.-N.; Zhang, T.-S.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Asian J. Org. Chem. 2020, 9, 1040. doi: 10.1002/ajoc.v9.7
	(e) Wei, W.-T.; Li, Q.; Zhang, M.-Z.; He, W.-M. Chin. J. Catal. 2021, 42, 731. doi: 10.1016/S1872-2067(20)63702-0
	(f) Zhang, T.-S.; Hao, W.-J.; Cai, P.-J.; Li, G.; Tu, S.-J.; Jiang, B. Front. Chem. 2020, 8, 234. doi: 10.3389/fchem.2020.00234
[10]	Shi, H.-N.; Huang, M.-H.; Hao, W.-J.; Tu, X.-C.; Tu, S.-J.; Jiang, B. J. Org. Chem. 2019, 84, 16027. doi: 10.1021/acs.joc.9b02525 pmid: 31769289
[11]	Shen, Z.-J.; Wang, S.-C.; Hao, W.-J.; Yang, S.-Z.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2019, 361, 3837. doi: 10.1002/adsc.v361.16
[12]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r
	(b) Zhu, C.-F.; Zhang, J.; Zhu, Y.-L.; Hao, W.-J.; Tu, S.-J.; Wang, D.-C.; Jiang, B. Org. Chem. Front. 2021, 8, 1952. doi: 10.1039/D1QO00124H
	(c) Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese) doi: 10.6023/cjoc202000041
	( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) doi: 10.6023/cjoc202000041
	(d) Peng, S.; Lin, Y.-W.; He, W.-M. Chin. J. Org. Chem. 2020, 40, 541. (in Chinese) doi: 10.6023/cjoc202000006
	( 彭莎, 林英武, 何卫民, 有机化学, 2020, 40, 541.) doi: 10.6023/cjoc202000006
	(e) Yi, R.; He, W. Chin. J. Org. Chem. 2021, 41, 1267. (in Chinese) doi: 10.6023/cjoc202100022
	( 易荣楠, 何卫民, 有机化学, 2021, 41, 1267.) doi: 10.6023/cjoc202100022
	(f) Chen, J.-R.; Hu, X. Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 2044. doi: 10.1039/C5CS00655D
	(g) Xuan, J.; Zhang, Z. G.; Xiao, W.-J. Angew. Chem. Int. Ed. 2015, 54, 15632. doi: 10.1002/anie.v54.52
	(h) Huang, H. C.; Jia, K. F.; Chen, Y. ACS Catal. 2016, 6, 4983. doi: 10.1021/acscatal.6b01379
	(i) Mi, X.; Kong, Y. F.; Zhang, J. Y.; Pi, C.; Cui, X. L. Chin. Chem. Lett. 2019, 30, 2295. doi: 10.1016/j.cclet.2019.09.040
[13]	(a) Zhu, S.-S.; Zhou, J.-N.; Wu, Q.-L.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Org. Chem. Front. 2020, 7, 2975. doi: 10.1039/D0QO00917B pmid: 31769294
	(b) Zhao, Q.; Hao, W.-J.; Shi, H.-N.; Xu, T.; Tu, S.-J.; Jiang, B. Org. Lett. 2019, 21, 9784. doi: 10.1021/acs.orglett.9b04018 pmid: 31769294
	(c) Gui, Q.-W.; Teng, F.; Li, Z.-C.; Xiong, Z.-Y.; Jin, X.-F.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 1907. doi: 10.1016/j.cclet.2021.01.021 pmid: 31769294
	(d) Liu, K.-J.; Wang, Z.; Lu, L.-H.; Chen, J.-Y.; Zeng, F.; Lin, Y.-W.; Cao, Z.; Yu, X.; He, W.-M. Green Chem. 2021, 23, 496. doi: 10.1039/D0GC02663H pmid: 31769294
[14]	(a) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030
	(b) Yang, Z.; Stivanin, M. L.; Jurberg, I. D.; Koenigs, R. M. Chem. Soc. Rev. 2020, 49, 6833. doi: 10.1039/D0CS00224K
	(c) Chen, D. M.; Sun, Y. Y.; Dong, D. Q.; Han, Q. Q.; Wang, Z. L. Chin. J. Org. Chem. 2020, 40, 4267. (in Chinese) doi: 10.6023/cjoc202006025
	( 陈德茂, 孙媛媛, 董道青, 韩晴晴, 王祖利, 有机化学, 2020, 40, 4267.) doi: 10.6023/cjoc202006025
	(d) 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
[15]	Wu, D.; Hao, W.-J.; Rao, Q.; Lu, Y.; Tu, S.-J.; Jiang, B. Chem. Commun. 2021, 57, 1911. doi: 10.1039/D0CC07880H
[16]	(a) Kharasch, M. S.; Jensen, E. V.; Urry, W. H. Science 1945, 102, 128. pmid: 17777366
	(b) Chen, B.; Fang, C.; Liu, P.; Ready, J. M. Angew. Chem., nt. Ed. 2017, 56, 8780. pmid: 17777366
	(c) Wang, L. L.; Zhang, M.; Zhang, Y. L.; Liu, Q. S.; Zhang, X. H.; Li, J. S.; Luo, Z. D.; Wei, W. Chin. Chem. Lett. 2020, 31, 67. doi: 10.1016/j.cclet.2019.05.041 pmid: 17777366
[17]	(a) Bacauanu, V.; Cardinal, S.; Yamauchi, M.; Kondo, M.; Fernandez, D. F.; Remy, R.; MacMillan, D. W. C. Angew. Chem., nt. Ed. 2018, 57, 12543.
	(b) Wang, S.-W.; Yu, J.; Zhou, Q.-Y.; Chen, S.-Y.; Xu, Z.-H. Tang, S. ACS Sustainable Chem. Eng. 2019, 7, 10154. doi: 10.1021/acssuschemeng.9b02178

Entry	Variation of the established conditions	Yield/%
1	None	85
2	4.0 Equiv. of BrCCl₃	80
3	3.0 Equiv. of BrCCl₃	41
4	AgSCF₃ instead of AgOAc	73
5	10 mol% of AgOAc	Trace
6	50 mol% of AgOAc	36
7	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	80
8	Eosin Y instead of fac-Ir(ppy)₃	67
9	Without fac-Ir(ppy)₃	0
10	No light	0
11	CH₃CN as solvent	72
12	THF as solvent	Trace
13	K₂CO₃ instead of NaOAc	64
14	CsCO₃ instead of NaOAc	68

Entry	Variation of the established conditions	Yield/%
1	None	85
2	4.0 Equiv. of BrCCl₃	80
3	3.0 Equiv. of BrCCl₃	41
4	AgSCF₃ instead of AgOAc	73
5	10 mol% of AgOAc	Trace
6	50 mol% of AgOAc	36
7	Ru(bpy)₃Cl₂•6H₂O instead of fac-Ir(ppy)₃	80
8	Eosin Y instead of fac-Ir(ppy)₃	67
9	Without fac-Ir(ppy)₃	0
10	No light	0
11	CH₃CN as solvent	72
12	THF as solvent	Trace
13	K₂CO₃ instead of NaOAc	64
14	CsCO₃ instead of NaOAc	68

可见光催化的1,6-烯炔参与的Kharasch加成反应

Visible-Light-Driven Photocatalytic Kharasch-Type Addition of 1,6-Enynes

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