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
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