研究论文

铜催化环状烯烃烯丙位C(sp3)—H磺酰化反应研究

  • 刘春阳 ,
  • 李燕 ,
  • 张前
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  • a 东北师范大学化学学院 长春 130024
    b 中国科学院上海有机化学研究所 金属有机化学国家重点实验室 上海 200032

收稿日期: 2022-11-24

  修回日期: 2023-02-16

  网络出版日期: 2023-03-01

基金资助

国家自然科学基金(22193012); 国家自然科学基金(21831002); 中央高校基本科研业务经费(2412022ZD049)

Copper-Catalyzed Allylic C(sp3)—H Sulfonylation of Cyclic Olefins

  • Chunyang Liu ,
  • Yan Li ,
  • Qian Zhang
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  • a Department of Chemistry, Northeast Normal University, Changchun 130024
    b State key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
* Corresponding authors. E-mail: ;

Received date: 2022-11-24

  Revised date: 2023-02-16

  Online published: 2023-03-01

Supported by

National Natural Science Foundation of China(22193012); National Natural Science Foundation of China(21831002); Fundamental Research Funds for the Central Universities(2412022ZD049)

摘要

发展了一种温和的铜催化烯丙位C(sp3)—H直接高效磺酰化方法, 以简单环状烯烃和亚磺酸钠为反应原料, 以中等至良好的收率合成了一系列烯丙基砜衍生物. 机理研究表明, 该反应可能经历了自由基中间体.

本文引用格式

刘春阳 , 李燕 , 张前 . 铜催化环状烯烃烯丙位C(sp3)—H磺酰化反应研究[J]. 有机化学, 2023 , 43(3) : 1091 -1101 . DOI: 10.6023/cjoc202211028

Abstract

A highly efficient copper-catalyzed direct sulfonylation of allylic C(sp3)—H bond was developed using simple cyclic olefins and sodium sulfite as starting materials. A series of allylic sulfone derivatives were synthesized in moderate to good yields under mild conditions. The mechanism study shows that the reaction might involve radical intermediates.

参考文献

[1]
(a) Mishra, N. K.; Sharma, S.; Park, J.; Han, S.; Kim, I. S. ACS Catal. 2017, 7, 2821.
[1]
(b) Orcel, U.; Waser, J. Chem. Sci. 2017, 8, 32.
[1]
(c) Koschker, P.; Breit, B. Acc. Chem. Res. 2016, 49, 1524.
[1]
(d) Kumar, D.; Vemula, S. R.; Balasubramanian, N.; Cook, G. R. Acc. Chem. Res. 2016, 49, 2169.
[1]
(e) Lu, Z.; Ma, S.-M. Angew. Chem., Int. Ed. 2008, 47, 258.
[2]
(a) Kazerouni, A. M.; McKoy, Q. A.; Blakey, S. B. Chem. Commun. 2020, 56, 13287.
[2]
(b) Manoharan, R.; Jeganmohan, M. Eur. J. Org. Chem. 2020, 7304.
[3]
(a) Knecht, T.; Mondal, S.; Ye, J.-H.; Das, M.; Glorius, F. Angew. Chem., Int. Ed. 2019, 58, 7117.
[3]
(b) Qi, X. -X.; Chen, P. -H.; Liu, G.-S. Angew. Chem., Int. Ed. 2017, 56, 9517.
[3]
(c) Osberger, T. J.; White, M. C. J. Am. Chem. Soc. 2014, 136, 11176.
[3]
(d) Reed, S. A.; White, M. C. J. Am. Chem. Soc. 2008, 130, 3316.
[3]
(e) Young, A. J.; White, M. C. J. Am. Chem. Soc. 2008, 130, 14090.
[3]
(f) Li, Z.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 56.
[4]
Huang, H.-M.; Bellotti, P.; Glorius, F. Chem. Soc. Rev. 2020, 49, 6186.
[5]
(a) Ide, T.; Feng, K.; Dixon, C. F.; Teng, D. W.; Clark, J. R.; Han, W.; Wendell, C. I.; Koch, V.; White, M. C. J. Am. Chem. Soc. 2021, 143, 14969.
[5]
(b) Liu, L.; Guo, K.-X.; Tian, Y.; Yang, C.-J.; Gu, Q.-S.; Li, Z.-L.; Ye, L.; Liu, X.-Y. Angew. Chem., Int. Ed. 2021, 60, 26710.
[5]
(c) Ye, L.; Tian, Y.; Meng, X.; Gu, Q.-S.; Liu, X.-Y. Angew. Chem., Int. Ed. 2020, 59, 1129.
[5]
(d) Li, J.-Y.; Zhang, Z.-H.; Wu, L.-Q.; Zhang, W.; Chen, P.-H.; Lin, Z.-Y.; Liu, G.-S. Nature 2019, 574, 516.
[5]
(e) Mitsunuma, H.; Tanabe, S.; Fuse, H.; Ohkubo, K.; Kanai, M. Chem. Sci. 2019, 10, 3459.
[5]
(f) Huang, L.; Rueping, M. Angew. Chem., Int. Ed. 2018, 57, 10333.
[5]
(g) Gephart III, R. T.; Huang, D. L.; Aguila, M. J. B.; Schmidt, G.; Shahu, A.; Warren, T. H. Angew. Chem., Int. Ed. 2012, 51, 6488.
[5]
(h) Andrus, M. B.; Zhou, Z.-N. J. Am. Chem. Soc. 2002, 124, 8806.
[6]
Huang, C.; Ci, R.-N.; Qiao, J.; Wang, X.-Z.; Feng, K.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Angew. Chem., Int. Ed. 2021, 60, 11779
[7]
(a) Chen, X.; Hussain, S.; Parveen, S.; Zhang, S.; Yang, Y.; Zhu, C. Curr. Med. Chem. 2012, 19, 3578.
[7]
(b) Back, T. G.; Clary, K. N.; Gao, D. Chem. Rev. 2010, 110, 4498.
[7]
(c) Reck, F.; Zhou, F.; Girardot, M.; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B. J. Med. Chem. 2005, 48, 499.
[8]
(a) Alba, A. R.; Companyo, X.; Rios, R. Chem. Soc. Rev. 2010, 39, 2018.
[8]
(b) Nielsen, M.; Jacobsen, C. B.; Holub, N.; Paixao, M. W.; J?rgensen, K. A. Angew. Chem., Int. Ed. 2010, 49, 2668.
[8]
(c) El-Awa, A.; NoShi, M. N.; Mollat du Jourdin, X.; Fuchs, P. L. Chem. Rev. 2009, 109, 2315.
[9]
(a) Salman, M.; Xu, Y.-Y.; Khan, S.; Zhang, J.-J.; Khan, A. Chem. Sci. 2020, 11, 5481.
[9]
(b) Cai, A.; Kleij, A. W. Angew. Chem., Int. Ed. 2019, 58, 14944.
[9]
(c) Wang, T.-T.; Wang, F.-X.; Yang, F.-L.; Tian, S.-K. Chem. Commun. 2014, 50, 3802.
[9]
(d) Wu, X.-S.; Chen, Y.; Li, M.-B.; Zhou, M.-G.; Tian, S.-K. J. Am. Chem. Soc. 2012, 134, 14694.
[9]
(e) Jegelka, M.; Plietker, B. ChemCatChem 2012, 4, 329.
[9]
(f) Ueda, M.; Hartwig, J. F. Org. Lett. 2010, 12, 92.
[9]
(g) Jegelka, M.; Plietker, B. Org. Lett. 2009, 11, 3462.
[9]
(h) Trost, B. M.; Crawley, M. L.; Lee, C. B. J. Am. Chem. Soc. 2000, 122, 6120.
[9]
(i) Trost, B. M.; Organ, M. G.; O'Doherty, G. A. J. Am. Chem. Soc. 1995, 117, 9662.
[10]
(a) Khakyzadeh, V.; Wang, Y.-H.; Breit, B. Chem. Commun. 2017, 53, 4966.
[10]
(b) Pritzius, A. B.; Breit, B. Angew. Chem., Int. Ed. 2015, 54, 15818.
[10]
(c) Pritzius, A. B.; Breit, B. Angew. Chem., Int. Ed. 2015, 54, 3121.
[10]
(d) Xu, K.; Khakyzadeh, V.; Bury, T.; Breit, B. J. Am. Chem. Soc. 2014, 136, 16124.
[11]
Zhang, J.; Zhou, K.; Qiu, G.; Wu, J. Org. Chem. Front. 2019, 6, 36.
[12]
(a) Long, J.; Shi, L.; Li, X.; Lv, H.; Zhang, X. Angew. Chem., Int. Ed. 2018, 57, 13248.
[12]
(b) Zhang, G.; Zhang, L.; Yi, H.; Luo, Y.; Qi, X.; Tung, C.-H.; Wu, L.-Z.; Lei, A.-W. Chem. Commun. 2016, 52, 10407.
[12]
(c) Mao, R.; Yuan, Z.; Zhang, R.; Ding, Y.; Fan, X.; Wu, J. Org. Chem. Front. 2016, 3, 1498.
[12]
(d) Li, J.; Qin, G.; Liu, Y.; Huang, H. Org. Chem. Front. 2016, 3, 259.
[12]
(e) Zhou, P.-X.; Ye, Y.-Y.; Zhao, L.-B.; Hou, J.-Y.; Kang, X.; Chen, D.-Q.; Tang, Q.; Zhang, J. Y.; Huang, Q.-X.; Zheng, L.; Ma, J.-W.; Xu, P.-F.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 16093.
[12]
(f) Li, X.; Xu, X.; Zhou, C. Chem. Commun. 2012, 48, 12240.
[13]
(a) Liu, C.-Y.; Shangguan, X.-Y.; Li, Y.; Zhang, Q. Chem. Sci. 2022, 13, 7886.
[13]
(b) Xiong, T.; Zhang, Q. Chem. Soc. Rev. 2021, 50, 8857.
[13]
(c) Yang, S.-B.; Wang, L.-H.; Zhang, H.-W.; Liu, C.-Y.; Zhang, L.-L.; Wang, X.-M.; Zhang, G.; Li, Y.; Zhang, Q. ACS Catal. 2019, 9, 716.
[13]
(d) Yang, S.-B.; Li, Y.; Zhang, Q. Chin. J. Org. Chem. 2019, 39, 2226. (in Chinese)
[13]
(杨胜彪, 李燕, 张前, 有机化学, 2019, 39, 2226.)
[13]
(e) Xiong, T.; Zhang, Q. Chem. Soc. Rev. 2016, 45, 3069.
[13]
(f) Sun, J.-Q.; Zheng, G.-F.; Xiong, T.; Zhang, Q.; Zhao, J. B.; Li, Y.; Zhang, Q. ACS Catal. 2016, 6, 3674.
[13]
(g) Zheng, G.-F.; Li, Y.; Han, J.-J.; Xiong, T.; Zhang, Q. Nat. Commun. 2015, 6, 7011.
[13]
(h) Zhang, H.-W.; Song, Y.-C.; Zhao, J.-B.; Zhang, J.-P.; Zhang, Q. Angew. Chem., Int. Ed. 2014, 53, 11079.
[13]
(i) Zhang, H.-W.; Pu, W.-Y.; Xiong, T.; Li, Y.; Zhou, X.; Sun, K.; Liu, Q.; Zhang, Q. Angew. Chem., Int. Ed. 2013, 52, 2529.
[13]
(j) Ni, Z.-K.; Zhang, Q.; Xiong, T.; Zheng, Y.-Y.; Li, Y.; Zhang, H.-W.; Zhang, J.-P.; Liu, Q. Angew. Chem., Int. Ed. 2012, 51, 1244.
[14]
Zhang, Q.; Wang, S.-M.; Zhang, Q.; Xiong, T.; Zhang, Q. ACS Catal. 2022, 12, 527.
[15]
(a) Zhou, X.-S.; Cheng, Y.; Chen, J.; Yu, X.-Y.; Xiao, W.-J.; Chen, J.-R. ChemCatChem 2019, 11, 5300.
[15]
(b) He, J.-Y.; Chen, G.-L.; Zhang, B.-X.; Li, Y.; Chen, J.-R.; Xiao, W.-J.; Liu, F.; Li, C.-Z. Chem 2020, 6, 1149.
[16]
(a) Jia, K.-F.; Zhang, F.-Y.; Huang, H.-C.; Chen, Y.-Y. J. Am. Chem. Soc. 2016, 138, 1514.
[16]
(b) Polák, P.; Tobrman, T. Eur. J. Org. Chem. 2019, 957.
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