Citation: Wang Lin, Yang Lili, Ou Yunfu, Xu Shihai, Lin Qifu, Yang Dingqiao. Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(12): 4228-4236. doi: 10.6023/cjoc202006074 shu

Platinum-Catalyzed syn-Stereocontrolled Ring-Opening of Oxabicyclic Alkenes with Arylsulfonyl Hydrazides

Wang Lin ^a,c,† ,
Yang Lili ^a,† ,
Ou Yunfu ^a ,
Xu Shihai ^a,b,, ,
Lin Qifu ^c ,
Yang Dingqiao ^c,,

a.
Analytical and Testing Center, Jinan University, Guangzhou 510632
b.
College of Chemistry and Materials Science, Jinan University, Guangzhou 510632
c.
School of Chemistry, South China Normal University, Guangzhou 510006

Corresponding author: Xu Shihai, txush@jnu.edu.c Yang Dingqiao, yangdq@scnu.edu.cn

^†

Received Date: 30 June 2020
Revised Date: 23 July 2020
Available Online: 18 August 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21672084, 21372090) and the Special Fund Project of Department of Natural Resources of Guangdong Province (Guangdong Natural Resources Cooperation) (No. 2020037)the National Natural Science Foundation of China 21672084the Special Fund Project of Department of Natural Resources of Guangdong Province (Guangdong Natural Resources Cooperation) 2020037the National Natural Science Foundation of China 21372090

Figures(3)

A platinum-catalyzed syn-stereocontrolled ring-opening reaction of oxabicyclic alkenes with arylsulfonyl hydrazides was developed. This protocol exhibited high efficiency and good functional group tolerance, affording cis-2-aryl-1, 2-dihydronaphthalen-1-ols (3) or 2-aryl-naphthalenes (4) as dehydrated products in good to excellent yields under mild conditions (up to 89%). In addition, the cis-1, 2-configuration of product (1S*, 2R*)-6, 7-dibromo-2-(p-tolyl)-1, 2-dihydronaphthalen-1-ol (3db) was confirmed by X-ray single crystal diffraction analysis. Based on the results, a plausible mechanism for the ring-opening reaction was proposed. Remarkably, arylsulfonyl hydrazides were used as carboanion nucleophiles in the ring-opening reaction via releasing N₂ and SO₂ in situ.
- platinum catalyst,
- ring-opening,
- oxabicyclic alkenes,
- arylsulfonyl hydrazides,
- nucleophiles
1. [1]
  (a) Ward, R. S. Chem. Soc. Rev. 1990, 19, 1.
  (b) Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169.
  (c) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
  (d) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
2. [2]
  (a) Lautens, M.; Fagnou, K.; Zunic, V. Org. Lett. 2002, 4, 3465.
  (b) McManus, H. A.; Fleming, M. J.; Lautens, M. Angew. Chem., Int. Ed. 2007, 46, 433.
  (c) Tsoung, J.; Krämer, K.; Zajdlik, A.; Liébert, C.; Lautens, M. J. Org. Chem. 2011, 76, 9031.
3. [3]
  (a) Yang, D.-Q.; Long, Y.-H.; Wang, H.; Zhang, Z.-M. Org. Lett. 2008, 10, 4723.
  (b) Long, Y.-H.; Li, X.-L.; Pan, X.-J.; Ding, D.-D.; Xu, X.; Zuo, X.-J.; Yang, D.-Q.; Wang, S.-Y.; Li, C.-R. Catal. Lett. 2014, 144, 419.
  (c) Yang, W.; Luo, R.-S.; Yang, D.-Q. Molecules 2015, 20, 21103.
  (d) Zhu, M.-N.; Chen, J.-C.; He, X.-B.; Gu, C.-P.; Xu, J.-B.; Fan, B.-M. J. Org. Chem. 2017, 82, 3167.
  (e) Yang, X.; Yang, W.; Yao, Y.-Q.; Deng, Y.-Y.; Zuo, X.-J.; Yang, D.-Q. J. Org. Chem. 2018, 83, 10097.
  (f) Yang, X.; Yang, W.; Yao, Y.-Q.; Deng, Y.-Y.; Yang, D.-Q. Org. Chem. Front. 2019, 6, 1151.
4. [4]
  (a) Rayabarapu, D. K.; Chiou, C.-F.; Cheng, C.-H. Org. Lett. 2002, 4, 1679.
  (b) Li, L.-P. Rayabarapu, D. K.; Nandi, M.; Cheng, C.-H. Org. Lett. 2003, 5, 1621.
  (c) Mannathana, S.; Cheng, C.-H. Adv. Synth. Catal. 2014, 356, 2239.
  (d) Shukla, P.; Sharma, A.; Pallavi, B.; Cheng, C.-H. Tetrahedron 2015, 71, 2260.
5. [5]
  (a) Cabrera, S.; Arrayás, R. G.; Carretero, J. C. Angew. Chem., Int. Ed. 2004, 43, 3944.
  (b) Zhang, T.-K.; Mo, D.-L.; Dai, L.-X.; Hou, X.-L. Org. Lett. 2008, 10, 3689.
  (c) Liu, S.-S.; Li, S.-F.; Chen, H.-L.; Yang, Q.-J.; Xu, J.-B.; Zhou, Y.-Y.; Yuan, M.-L.; Zeng, W.-M.; Fan, B.-M. Adv. Synth. Catal. 2014, 356, 2960.
  (d) Li, S.-F.; Xu, J.-B.; Fan, B.-M.; Lu, Z.-W.; Zeng, C.-Y.; Bian, Z.-X.; Zhou, Y.-Y.; Wang, J. Chem.-Eur. J. 2015, 21, 9003.
  (e) Lu, Z.-W.; Wang, J.; Han, B.-Q.; Li, S.-F.; Zhou, Y.-Y.; Fan, B.-M. Adv. Synth. Catal. 2015, 357, 3121.
  (f) Zhou, H.; Li, J.-X.; Yang, H.-M.; Xia, C.-G.; Jiang, G.-X. Org. Lett. 2015, 17, 4628.
  (g) Yang, F.; Chen, J.-C.; Xu, J.-B.; Ma, F.-J.; Zhou, Y.-Y.; Shinde, M. V.; Fan, B.-M. Org. Lett. 2016, 18, 4832.
6. [6]
  (a) Bertozzi, F.; Pineschi, M.; Macchia, F.; Arnold, L. A.; Minnaard, A. J.; Feringa, B. L. Org. Lett. 2002, 4, 2703.
  (b) Arrayas, R. G.; Cabrera, S.; Carretero, J. C. Org. Lett. 2005, 7, 219.
  (c) Zhang, W.; Wang, L.-X.; Shi, W.-J.; Zhou, Q.-L. J. Org. Chem. 2005, 70, 3734.
  (d) Zhang, W.; Zhu, S.-F.; Qiao, X.-C.; Zhou, Q.-L. Chem.-Asian J. 2008, 3, 2105.
  (e) Millet, R.; Bernardez, T.; Palais, L.; Alexakis, A. Tetrahedron Lett. 2009, 50, 3474.
  (f) Millet, R.; Gremaud, L.; Bernardez, T.; Palais, L.; Alexakis, A. Synthesis 2009, 12, 2101.
  (g) Bos, P. H.; Rudolph, A.; Pérez, M.; Fañanás-Mastral, M.; Harutyunyan, S. R.; Feringa, B. L. Chem. Commun. 2012, 48, 1748.
7. [7]
  (a) Leong, P.; Lautens, M. J. Org. Chem. 2004, 69, 2194.
  (b) Cho, Y.-H.; Zunic, V.; Senboku, H.; Olsen, M.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 6837.
  (c) Nishimura, T.; Tsurumaki, E.; Kawamoto, T.; Guo, X.-X.; Hayashi, T. Org. Lett. 2008, 10, 4057.
  (d) Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 5400.
  (e) Zhu, J.-T.; Tsui, G. C.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 12353.
  (f) Tsui, G. C.; Ninnemann, N. M.; Hosotani, A.; Lautens, M. Org. Lett. 2013, 5, 1064.
  (g) Zhang, L.; Le, C. M.; Lautens, M. Angew. Chem., Int. Ed. 2014, 53, 5951.
  (h) Chen, J.-C.; Zou, L.-L.; Zeng, C.-Y.; Zhou, Y.-Y.; Fan, B.-M. Org. Lett. 2018, 20, 1283.
8. [8]
  (a) Meng, L.; Yang, W.; Pan, X.-J.; Tao, M.; Cheng, G.; Wang, S.-Y.; Zeng, H.-P.; Long, Y.-H.; Yang, D.-Q. J. Org. Chem. 2015, 80, 2503.
  (b) Pan, X.-J.; Huang, G.-B.; Long, Y.-H.; Zuo, X.-J.; Xu, X.; Gu, F.-L.; Yang, D.-Q. J. Org. Chem. 2014, 79, 187.
9. [9]
  (a) Villeneuve, K.; Tam, W. J. Am. Chem. Soc. 2006, 128, 3514.
  (b) Tenaglia, A.; Marc, S.; Giordano, L.; De Riggi, I. Angew. Chem., Int. Ed. 2011, 50, 9062.
10. [10]
  Ito, S.; Itoh, T.; Nakamura, M. Angew. Chem., Int. Ed. 2011, 50, 454. doi: 10.1002/anie.201006180
11. [11]
  (a) Sawama, Y.; Kawamoto, K.; Satake, H.; Krause, N.; Kita, Y. Synlett 2010, 2151.
  (b) Huang, Y.; Ma, C.; Lee, Y. X.; Huang, R.-Z.; Zhao, Y. Angew. Chem., Int. Ed. 2015, 54, 13696.
12. [12]
  (a) Zeng, C.-Y.; Yang, F.; Chen, J.-C.; Wang, J.; Fan, B.-M. Org. Biomol. Chem. 2015, 13, 8425.
  (b) Xu, X.; Chen, J.-C.; He, Z.-X.; Zhou, Y.-Y.; Fan, B.-M. Org. Biomol. Chem. 2016, 14, 2480.
  (c) Yang, W.; Cheng, G.; Li, Y.; Zuo, X.-J.; Yang, D.-Q. Synthesis 2017, 49, 2025.
  (d) Shen, G.-L.; Khan, R.; Lv, H.-P.; Yang, Y.; Zhang, X.; Zhan, Y.; Zhou, Y.-Y.; Fan, B.-M. Org. Chem. Front. 2019, 6, 1423.
13. [13]
  (a) Cheng, H.-C.; Yang, D.-Q. J. Org. Chem. 2012, 77, 9756.
  (b) Fang, S.; Liang, X.-L.; Long, Y.-H.; Li, X.-L.; Yang, D.-Q.; Wang, S.-Y.; Li, C.-R. Organometallics 2012, 31, 3113.
14. [14]
  Yang, D.-Q.; Xia, J.-Y.; Long, Y.-H.; Zeng, Z.-Y.; Zuo, X.-J.; Wang, S.-Y.; Li, C.-R. Org. Biomol. Chem. 2013, 11, 4871. doi: 10.1039/c3ob40891d
15. [15]
  (a) Yang, D.-Q.; Liang, N. Org. Biomol. Chem. 2014, 12, 2080.
  (b) Chen, G.; Yang, W.; Li, Y.; Yang, D.-Q. J. Org. Chem. 2016, 81, 7817.
16. [16]
  Deng, Y.-Y.; Yang, W.; Yao, Y.-Q.; Yang, X.; Zuo, X.-J.; Yang, D.-Q. Org. Biomol. Chem. 2019, 17, 703. doi: 10.1039/C8OB02864H
17. [17]
  (a) Li, Y.; Yang, W.; Cheng, G.; Yang, D.-Q. J. Org. Chem. 2016, 81, 4744.
  (b) Wu, R.-H.; Yang, W.; Chen, W.-K.; Yang, D.-Q. Org. Chem. Front. 2017, 4, 1921.
18. [18]
  (a) Zeng, Z.-Y.; Yang, D.-Q.; Long, Y.-H.; Pan, X.-J.; Huang, G.-B.; Zuo, X.-J.; Zhou, W. J. Org. Chem. 2014, 79, 5249.
  (b) Zhang, W.; Chen, J.-C.; Zeng, G.-Z.; Yang, F.; Xu, J.-B.; Sun, W.-Q.; Shinde, M. V.; Fan, B.-M. J. Org. Chem. 2017, 82, 2641.
19. [19]
  Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507. doi: 10.1021/jo9710137
20. [20]
  Aziz, J.; Messaoudi, S.; Alami, M.; Hamze, A. Org. Biomol. Chem. 2014, 12, 9743. doi: 10.1039/C4OB01727G
21. [21]
  Chen, D.-H.; Yao, Y.-Q.; Yang, W.; Lin, Q.-F.; Li, H.-Y.; Wang, L.; Chen, S.-Q.; Tan, Y.; Yang, D.-Q. J. Org. Chem. 2019, 84, 12481. doi: 10.1021/acs.joc.9b01957
1. [1]
  Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
2. [2]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
3. [3]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
4. [4]
  Yizhe Chen , Yuzhou Jiao , Liangyu Sun , Cheng Yuan , Qian Shen , Peng Li , Shiming Zhang , Jiujun Zhang . Nonmetallic phosphorus alloying to regulate the oxygen reduction mechanisms of platinum catalyst. Chinese Chemical Letters, 2025, 36(4): 110789-. doi: 10.1016/j.cclet.2024.110789
5. [5]
  Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H₂O₂ system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
6. [6]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
7. [7]
  Sanmei Wang , Dengxin Yan , Wenhua Zhang , Liangbing Wang . Graphene-supported isolated platinum atoms and platinum dimers for CO₂ hydrogenation: Catalytic activity and selectivity variations. Chinese Chemical Letters, 2025, 36(4): 110611-. doi: 10.1016/j.cclet.2024.110611
8. [8]
  Zhenkang Ai , Hui Chen , Xuebin Liao . Nickel-catalyzed decarboxylative difluoromethylation and alkylation of alkenes. Chinese Chemical Letters, 2025, 36(3): 109954-. doi: 10.1016/j.cclet.2024.109954
9. [9]
  Kun Tang , Fen Su , Shijie Pan , Fengfei Lu , Zhongfu Luo , Fengrui Che , Xingxing Wu , Yonggui Robin Chi . Enones from aldehydes and alkenes by carbene-catalyzed dehydrogenative couplings. Chinese Chemical Letters, 2024, 35(9): 109495-. doi: 10.1016/j.cclet.2024.109495
10. [10]
  Er-Meng Wang , Ziyi Wang , Xu Ban , Xiaowei Zhao , Yanli Yin , Zhiyong Jiang . Chemoselective photocatalytic sulfenylamination of alkenes with sulfenamides via energy transfer. Chinese Chemical Letters, 2024, 35(12): 109843-. doi: 10.1016/j.cclet.2024.109843
11. [11]
  Bingbing Shi , Yuchun Wang , Yi Zhou , Xing-Xing Zhao , Yizhou Li , Nuoqian Yan , Wen-Juan Qu , Qi Lin , Tai-Bao Wei . A supramolecular oligo[2]rotaxane constructed by orthogonal platinum(Ⅱ) metallacycle and pillar[5]arene-based host–guest interactions. Chinese Chemical Letters, 2024, 35(10): 109540-. doi: 10.1016/j.cclet.2024.109540
12. [12]
  Pingping HAO , Fangfang LI , Yawen WANG , Houfen LI , Xiao ZHANG , Rui LI , Lei WANG , Jianxin LIU . Hydrogen production performance of the non-platinum-based MoS₂/CuS cathode in microbial electrolytic cells. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1811-1824. doi: 10.11862/CJIC.20240054
13. [13]
  Boqiang Wang , Yongzhuo Xu , Jiajia Wang , Muyang Yang , Guo-Jun Deng , Wen Shao . Transition-metal free trifluoromethylimination of alkenes enabled by direct activation of N-unprotected ketimines. Chinese Chemical Letters, 2024, 35(9): 109502-. doi: 10.1016/j.cclet.2024.109502
14. [14]
  Yunqiang Li , Yongxian Huang , Sinuo Li , He Huang , Zhiwei Jiao . Elaborating azaaryl alkanes enabled by photoredox/palladium dual catalyzed dialkylation of azaaryl alkenes. Chinese Chemical Letters, 2025, 36(4): 110051-. doi: 10.1016/j.cclet.2024.110051
15. [15]
  Hong Yin , Zhipeng Yu . Hexavalent iridium catalyst enhances efficiency of hydrogen production. Chinese Journal of Structural Chemistry, 2025, 44(1): 100382-100382. doi: 10.1016/j.cjsc.2024.100382
16. [16]
  Xiao-Ming Chen , Lianhui Song , Jun Pan , Fei Zeng , Yi Xie , Wei Wei , Dong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112
17. [17]
  Huaixiang Yang , Miao-Miao Li , Aijun Zhang , Jiefei Guo , Yongqi Yu , Wei Ding . Visible-light-induced photocatalyst- and metal-free radical phosphinoyloximation of alkenes with tert-butyl nitrite as bifunctional reagent. Chinese Chemical Letters, 2025, 36(3): 110425-. doi: 10.1016/j.cclet.2024.110425
18. [18]
  Qijun Tang , Wenguang Tu , Yong Zhou , Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170
19. [19]
  Zimo Peng , Quan Zhang , Gaocan Qi , Hao Zhang , Qian Liu , Guangzhi Hu , Jun Luo , Xijun Liu . Nanostructured Pt@RuOx catalyst for boosting overall acidic seawater splitting. Chinese Journal of Structural Chemistry, 2024, 43(1): 100191-100191. doi: 10.1016/j.cjsc.2023.100191
20. [20]
  Zhenzhen Zhao , Meichen Jiao , Jiejie Ling , Han Jiang , Yan Gao , Hao Xu , Hai-Qing Li , Jingang Jiang , Peng Wu , Le Xu . Toward the microporous zeolite family with tunable large-medium cage and pore opening. Chinese Journal of Structural Chemistry, 2024, 43(9): 100336-100336. doi: 10.1016/j.cjsc.2024.100336

Get Citation

PDF

XML

Metrics

PDF Downloads(62)
Abstract views(3094)
HTML views(448)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142