Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (11): 3900-3906.DOI: 10.6023/cjoc202304011 Previous Articles Next Articles
收稿日期:
2023-04-08
修回日期:
2023-06-25
发布日期:
2023-07-12
基金资助:
Duoduo Xiao, Jiantao Zhang, Peng Zhou(), Weibing Liu()
Received:
2023-04-08
Revised:
2023-06-25
Published:
2023-07-12
Contact:
E-mail: Supported by:
Share
Duoduo Xiao, Jiantao Zhang, Peng Zhou, Weibing Liu. Metal-Free α-C(sp3)—H Methylenation of Aryl Ketones to Form γ-Keto Sulfoxides with Dimethyl Sulfoxide[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3900-3906.
Entry | Peroxide | T/℃ | t/h | Yieldb/% |
---|---|---|---|---|
1 | (NH4)2S2O8 | 120 | 5 | 49 |
2 | (NH4)2S2O8 | 120 | 7 | 69 |
3 | (NH4)2S2O8 | 120 | 9 | 69 |
4 | (NH4)2S2O8 | 70 | 7 | — |
5 | (NH4)2S2O8 | r.t. | 7 | — |
6 | Benzoyl peroxide | 120 | 7 | — |
7 | Peroxide isobutylbenzene | 120 | 7 | — |
8 | K2S2O8 | 120 | 7 | 15 |
9 | DTBP | 120 | 7 | — |
10 | TBHP | 120 | 7 | — |
11c | (NH4)2S2O8 | 120 | 7 | 54 |
12d | (NH4)2S2O8 | 120 | 7 | 77 |
13d,e | (NH4)2S2O8 | 120 | 7 | 77 |
14d,f | (NH4)2S2O8 | 120 | 7 | 77 |
Entry | Peroxide | T/℃ | t/h | Yieldb/% |
---|---|---|---|---|
1 | (NH4)2S2O8 | 120 | 5 | 49 |
2 | (NH4)2S2O8 | 120 | 7 | 69 |
3 | (NH4)2S2O8 | 120 | 9 | 69 |
4 | (NH4)2S2O8 | 70 | 7 | — |
5 | (NH4)2S2O8 | r.t. | 7 | — |
6 | Benzoyl peroxide | 120 | 7 | — |
7 | Peroxide isobutylbenzene | 120 | 7 | — |
8 | K2S2O8 | 120 | 7 | 15 |
9 | DTBP | 120 | 7 | — |
10 | TBHP | 120 | 7 | — |
11c | (NH4)2S2O8 | 120 | 7 | 54 |
12d | (NH4)2S2O8 | 120 | 7 | 77 |
13d,e | (NH4)2S2O8 | 120 | 7 | 77 |
14d,f | (NH4)2S2O8 | 120 | 7 | 77 |
[1] |
(a) Sang, P.; Chen, Q.; Wang, D.-Y.; Guo, W.; Fu, Y. Chem. Rev. 2023, 123, 1260.
|
(b) Engel, S.; Fritz, E. C.; Ravoo, B. J. Chem. Soc. Rev. 2017, 46, 2057.
doi: 10.1039/C7CS00023E |
|
(c) Otocka, S.; Kwiatkowska, M.; Madalińska, L.; Kiełbasiński, P. Chem. Rev. 2017, 117, 4147.
doi: 10.1021/acs.chemrev.6b00517 |
|
[2] |
(a) Feng, M.; Mosiagin, I.; Kaiser, D.; Maryasin, B.; Maulide, N. J. Am. Chem. Soc. 2022, 144, 13044.
doi: 10.1021/jacs.2c05368 |
(b) Huang, X.; Maulide, N. J. Am. Chem. Soc. 2011, 133, 8510.
doi: 10.1021/ja2031882 |
|
[3] |
(a) Bugaenko, D. I.; Volkov, A. A.; Andreychev, V. V.; Karchava, A. V. Org. Lett. 2023, 25, 272.
doi: 10.1021/acs.orglett.2c04143 pmid: 36594721 |
(b) Kaiser, D.; Klose, I.; Oost, R.; Neuhaus, J.; Maulide, N. Chem. Rev. 2019, 119, 8701.
doi: 10.1021/acs.chemrev.9b00111 pmid: 36594721 |
|
(c) Vizer, S. A.; Sycheva, E. S.; Al Quntar, A. A. A.; Kurmankulov, N. B.; Yerzhanov, K. B.; Dembitsky, V. M. Chem. Rev. 2015, 115, 1475.
doi: 10.1021/cr4001435 pmid: 36594721 |
|
[4] |
(a) Wu, Y. H.; Wang, N. X.; Zhang, T.; Yan, Z.; Xu, B. C.; Inoa, J.; Xing, Y. Adv. Synth. Catal. 2019, 361, 3008.
doi: 10.1002/adsc.v361.12 |
(b) Song, S.; Huang, X.; Liang, Y. F.; Tang, C.; Li, X.; Jiao, N. Green Chem. 2015, 17, 2727.
doi: 10.1039/C5GC00184F |
|
[5] |
(a) Yadav, P.; Awasthi, A; Gokulnath, S.; Tiwari, D. K. J. Org. Chem. 2021, 86, 2658.
doi: 10.1021/acs.joc.0c02696 |
(b) Phanindrudu, M.; Wakade, S. B.; Tiwari, D. K.; Likhar, P. R.; Tiwari, D. K. J. Org. Chem. 2018, 83, 9137.
doi: 10.1021/acs.joc.8b01204 |
|
(c) Wu, X.; Zhang, J.; Liu, S.; Gao, Q.; Wu, A. Adv. Synth. Catal. 2016, 358, 218.
doi: 10.1002/adsc.v358.2 |
|
[6] |
(a) Tian, Y.; Zhang, J.; Gao, W.; Chang, H. Chin. J. Org. Chem. 2023, 43, 2391. (in Chinese)
doi: 10.6023/cjoc202211026 |
(田钰, 张娟, 高文超, 常宏宏, 有机化学, 2023, 43, 2391.)
doi: 10.6023/cjoc202211026 |
|
(b) Xu, C.; Jiang, S. F.; Wen, X. H.; Zhang, Q.; Zhou, Z. W.; Wu, Y. D.; Jia, F. C.; Wu, A. X. Adv. Synth. Catal. 2018, 360, 2267.
doi: 10.1002/adsc.v360.12 |
|
[7] |
(a) Wang, M.; Tang, B. C.; Ma, J. T.; Wang, Z. X.; Xiang, J. C.; Wu, Y. D.; Wang, J. G.; Wu, A. X. Org. Biomol. Chem. 2019, 17, 1535.
doi: 10.1039/C8OB02994F |
(b) Liu, Y.; Hu, Y.; Cao, Z.; Zhan, X.; Luo, W.; Liu, Q.; Guo, C. Adv. Synth. Catal. 2019, 361, 1084.
doi: 10.1002/adsc.v361.5 |
|
[8] |
(a) Jiang, Y.; Loh, T. P. Chem. Sci. 2014, 5, 4939.
doi: 10.1039/C4SC01901F |
(b) Yuan, G.; Zheng, J.; Gao, X.; Li, X.; Huang, L.; Chen, H.; Jiang, H. Chem. Commun. 2012, 48, 7513.
doi: 10.1039/c2cc32964f |
|
[9] |
(a) Lin, Z.; Huang, L.; Yuan, G. Chem. Commun. 2021, 57, 3579.
doi: 10.1039/D1CC00026H |
(b) Xu, N.; Zhang, Y.; Chen, W.; Li, P.; Wang, L. Adv. Synth. Catal. 2018, 360, 1199.
doi: 10.1002/adsc.v360.6 |
|
(c) Wen, Z. K.; Liu, X. H.; Liu, Y. F.; Chao, J. B. Org. Lett. 2017, 19, 5798.
doi: 10.1021/acs.orglett.7b02753 |
|
[10] |
(a) Liu, Y.; Zhan, X.; Ji, P.; Xu, J.; Liu, Q.; Luo, W.; Chen, T.; Guo, C. Chem. Commun. 2017, 53, 5346.
doi: 10.1039/C7CC01309D pmid: 26646089 |
(b) Shen, T.; Huang, X.; Liang, Y. F.; Jiao, N. Org. Lett. 2015, 17, 6186.
doi: 10.1021/acs.orglett.5b03179 pmid: 26646089 |
|
[11] |
(a) Chang, M.Y.; Chen, H.Y.; Tsai, Y. L. Org. Lett. 2019, 21, 1832.
doi: 10.1021/acs.orglett.9b00422 |
(b) Sun, K.; Zhu, Z.; Sun, J.; Liu, L.; Wang, X. J. Org. Chem. 2016, 81, 1476.
doi: 10.1021/acs.joc.5b02593 |
|
(c) Jia, T.; Bellomo, A.; Baina, K. E. L.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2013, 135, 3740.
doi: 10.1021/ja4009776 |
|
[12] |
(a) Gupta, A.; Rahaman, A.; Bhadra, S. Org. Lett. 2019, 21, 6164.
doi: 10.1021/acs.orglett.9b02424 |
(b) Wu, Y.; Huang, Z.; Luo, Y.; Liu, D.; Deng, Y.; Yi, H.; Lee, J. F.; Pao, C. W.; Chen, J. L.; Lei, A. Org. Lett. 2017, 19, 2330.
doi: 10.1021/acs.orglett.7b00865 |
|
[13] |
(a) Zhu, J.; Guo, Y.; Zhang, Y.; Li, W.; Zhang, P.; Xu, J. Green Chem. 2023, 25, 986.
doi: 10.1039/D2GC04521D |
(b) Xu, J.; Liang, C.; Shen, J.; Chen, Q.; Li, W.; Zhang, P. Green Chem. 2023, 25, 1975.
doi: 10.1039/D2GC04909K |
|
(c) Xu, J.; Huang, L.; He, L.; Liang, C.; Ouyang, Y.; Shen, J.; Jiang, M.; Li, W. Green Chem. 2021, 23, 6632.
doi: 10.1039/D1GC01899J |
|
(d) Xu, J.; He, L.; Liang, C.; Yue, X.; Ouyang, Y.; Zhang, P. ACS Sustainable Chem. Eng. 2021, 9, 13663.
doi: 10.1021/acssuschemeng.1c05237 |
|
[14] |
(a) Lu, M.; Qin, H.; Lin, Z.; Huang, M.; Weng, W.; Cai, S. Org. Lett. 2018, 20, 7611.
doi: 10.1021/acs.orglett.8b03340 |
(b) Budén, M. E.; Bardagí, J. I.; Puiatti, M.; Rossi, R. A. J. Org. Chem. 2017, 82, 8325.
doi: 10.1021/acs.joc.7b00822 |
|
[15] |
(a) Singsardar, M.; Laru, S.; Mondal, S.; Hajra, A. J. Org. Chem. 2019, 84, 4543.
doi: 10.1021/acs.joc.9b00318 pmid: 30875224 |
(b) Zhang, R.; Jin, S.; Liu, Q.; Lin, S.; Yan, Z. J. Org. Chem. 2018, 83, 13030.
doi: 10.1021/acs.joc.8b01508 pmid: 30875224 |
|
(c) Ji, X.; Li, D.; Zhou, X.; Huang, H.; Deng, G. J. Green Chem. 2017, 19, 619.
doi: 10.1039/C6GC02271E pmid: 30875224 |
|
(d) Xu, Z.; Hang, Z.; Chai, L.; Liu, Z. Q. Org. Lett. 2016, 18, 4662.
doi: 10.1021/acs.orglett.6b02274 pmid: 30875224 |
|
(e) Wu, X.; Zhao, Y.; Ge, H. Chem. Sci. 2015, 6, 5978.
doi: 10.1039/C5SC02143J pmid: 30875224 |
|
(f) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111,1780.
doi: 10.1021/cr100379j pmid: 30875224 |
|
(g) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
doi: 10.1021/cr100280d pmid: 30875224 |
|
(h) Li, C. J. Acc. Chem. Res. 2009, 42, 335.
doi: 10.1021/ar800164n pmid: 30875224 |
|
[16] |
(a) Tong, H.; Chen, C.; Liu, W.; Pan, Y.; Duan, L. Asian J. Org. Chem. 2019, 8, 479.
doi: 10.1002/ajoc.v8.4 |
(b) Liu, W.; Tan, H.; Chen, C.; Pan, Y. Adv. Synth. Catal. 2017, 359, 1594.
doi: 10.1002/adsc.v359.9 |
|
(c) Chen, C.; Liu, W.; Zhou, P.; Liu, H. RSC Adv. 2017, 7, 20394.
doi: 10.1039/C7RA02298K |
|
[17] |
(a) Tan, L.; Chen, C.; Liu, W. Beilstein J. Org. Chem. 2017, 13, 1079.
doi: 10.3762/bjoc.13.107 |
(b) Xu, K.; Fang, Y.; Yan, Z.; Zha, Z.; Wang, Z. Org. Lett. 2013, 15, 2148.
doi: 10.1021/ol4006344 |
|
[18] |
(a) Liu, Y.; Wang, Q. L.; Chen, Z.; Zhou, Q.; Li, H.; Xu, W. Y.; Xiong, B. Q.; Tang, K. W. J. Org. Chem. 2019, 84, 5413.
doi: 10.1021/acs.joc.9b00407 pmid: 30908920 |
(b) Li, C.; Jin, T.; Zhang, X.; Li, C.; Jia, X.; Li, J. Org. Lett. 2016, 18, 1916.
doi: 10.1021/acs.orglett.6b00749 pmid: 30908920 |
|
[19] |
Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 119, 525.
doi: 10.1007/s00214-007-0401-8 |
[20] |
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.02, Gaussian, Inc., Wallingford, CT, 2009.
|
[1] | Yatong Fu, Chaofan Sun, Dan Zhang, Chengguo Jin, Juyou Lu. Recent Progress in B—H Bond Functionalization of nido-Carboranes [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 438-447. |
[2] | Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348. |
[3] | Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437. |
[4] | Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583. |
[5] | Jianghu Dong, Liangming Xuan, Chi Wang, Chenxi Zhao, Haifeng Wang, Qiongjiao Yan, Wei Wang, Fen'er Chen. Recent Advances in Visible-Light-Induced C(3)—H Functionalization of Quinoxalinones under Transition-Metal-Free or Photocatalyst-Free [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 111-136. |
[6] | Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147. |
[7] | Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446. |
[8] | Yijun Shi, Xinyue Sun, Han Cao, Fusheng Bie, Jie Ma, Zhe Liu, Xingshun Cong. Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2499-2505. |
[9] | Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244. |
[10] | Jiao Qin, Jie Chen, Yan Su. Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2171-2177. |
[11] | Jian Ji, Jinhua Liu, Cong Guan, Xuwen Chen, Yun Zhao, Shunying Liu. High Regioselective Synthesis of N2-Substituted-1,2,3-triazole via N-Sulfonyl-1,2,3-triazole Coupling with Alcohol Catalyzed by in-situ Generated Sulfonic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1168-1176. |
[12] | Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145. |
[13] | Biao Ma, Miaomiao Zhang, Zhanyu Li, Jinsong Peng, Chunxia Chen. Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 455-470. |
[14] | Jing Sun, Mengmeng Zhang, Xiaolong Guo, Qi Wang, Luyao Wang. Synthesis of Diaryl Selenium Compounds without Transition-Metal Catalyst [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4251-4260. |
[15] | Peng Zhou, Weiming Zhu, Jiantao Zhang, Duoduo Xiao, Xiangfeng Guo, Weibing Liu. Cobalt-Catalyzed Oxyalkylation Reaction of Styrenes: Rapid Access to α-Alkyl Substituted Acetophenone Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3939-3944. |
Viewed | ||||||
Full text |
|
|||||
Abstract |
|
|||||