NOTES

Nickel-Catalyzed Heck Reaction of Cycloalkenes with Inert C—O Bonds of Aryl Carbonates and Aryl Sulfamates

  • Xuqun Zeng ,
  • Qian Zhang ,
  • Xufeng Wu ,
  • Jingfeng Zhang ,
  • Xinwei Zhang ,
  • Xiaolei Huang
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  • Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004
* Corresponding author. E-mail:

Received date: 2022-04-14

  Revised date: 2022-05-20

  Online published: 2022-06-09

Supported by

Zhejiang Provincial Natural Science Foundation(LQ22B020002)

Abstract

An efficient nickel-catalyzed Heck reaction of cycloalkenes with inert C—O bonds of aryl carbonates and sulfamates has been developed. Naphthyl, heterocycles and simple phenyl substituted carbonates with various functional groups are compatible with the catalytic systems comprising Ni(II), PhBPE ligand and reductive metal Zn.

Cite this article

Xuqun Zeng , Qian Zhang , Xufeng Wu , Jingfeng Zhang , Xinwei Zhang , Xiaolei Huang . Nickel-Catalyzed Heck Reaction of Cycloalkenes with Inert C—O Bonds of Aryl Carbonates and Aryl Sulfamates[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2981 -2987 . DOI: 10.6023/cjoc202204034

References

[1]
For selected reviews, see: (a) Zheng, Y.-L.; Newman, S. G.. Chem. Commun. 2021, 57, 2591.
[1]
(b) Clevenger, A. L.; Stolley, R. M.; Aderibigbe, J.; Louie, J. Chem. Rev. 2020, 120, 6124.
[1]
(c) Boit, T. B.; Bulger, A. S.; Dander, J. E.; Garg, N. K. ACS Catal. 2020, 10, 12109.
[1]
(d) Cheng, L.; Zhou, Q. Acta Chim. Sinica 2020, 78, 1017. (in Chinese)
[1]
(程磊, 周其林, 化学学报, 2020, 78, 1017.)
[1]
(e) Wu, L.; Wei, H.; Shen, J.; Chen, J.; Zhang, W. Acta Chim. Sinica 2021, 79, 1331. (in Chinese)
[1]
(吴良, 魏瀚林, 申杰峰, 陈建中, 张万斌, 化学学报, 2021, 79, 1331.)
[1]
(f) Liang, L.; Zhang, L.; Peng, Y.; Liu, H. Chin. J. Org. Chem. 2022, 42, 1033. (in Chinese)
[1]
(梁陆祺, 张立志, 彭永利, 刘会, 有机化学, 2022, 42, 1033.)
[2]
For selected reviews, see: (a) Qiu, Z.; Li, C.-J. Chem. Rev. 2020, 120, 10454.
[2]
(b) Han, F.-S. Chem. Soc. Rev. 2013, 42, 5270.
[2]
(c) Mesganaw, T.; Garg, N. K. Org. Process Res. Dev. 2013, 17, 29.
[2]
(d) Rosen, B. M.; Quasdorf, K. W.; Wilson, D. A.; Zhang, N.; Resmerita, A.-M.; Garg, N. K.; Percec, V. Chem. Rev. 2011, 111, 1346.
[2]
(e) Li, B.-J.; Yu, D.-G.; Sun, C.-L.; Shi, Z.-J. Chem.-Eur. J. 2011, 17, 1728.
[3]
For selected examples, see: (a) Hong, X.; Liang, Y.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 2017.
[3]
(b) Uthayopas, C.; Surawatanawong, P. Dalton Trans. 2019, 48, 7817.
[3]
(c) Gan, Y.; Wang, G.; Xie, X.; Liu, Y. J. Org. Chem. 2018, 83, 14036.
[3]
(d) Takise, R.; Itami, K.; Yamaguchi, J. Org. Lett. 2016, 18, 4428.
[3]
(e) Yang, J.; Chen, T.; Han, L.-B. J. Am. Chem. Soc. 2015, 137, 1782.
[3]
(f) Yu, D.-G.; Li, B.-J.; Shi, Z.-J. Acc. Chem. Res. 2010, 43, 1486.
[4]
Rappoport, Z. The Chemistry of Phenols, Wiley: Chichester, U. K., 2003.
[5]
(a) Peng, Y.; Han, C.; Luo, Y.; Li, G.; Huo, X.; Zhang, W. Angew. Chem. Int. Ed. 2022, 61, e202203448.
[5]
(b) Gupta, A.; Kumar, J.; Bhadra, S. Org. Biomol. Chem. 2018, 16, 3716.
[6]
Quasdorf, K. W.; Riener, M.; Petrova, K. V.; Garg, N. K. J. Am. Chem. Soc. 2009, 131, 17748.
[7]
Kuwano, R.; Shimizu, R. Chem. Lett., 2011, 40, 913.
[8]
Guo, L.; Hsiao, C.-C.; Yue, H.; Liu, X.; Rueping, M. ACS Catal. 2016, 6, 4438.
[9]
Purohit, P.; Seth, K.; Kumar, A.; Chakraborti, A. K. ACS Catal. 2017, 7, 2452.
[10]
Yue, H.; Guo, L.; Liu, X.; Rueping, M. Org. Lett. 2017, 19, 1788.
[11]
For selected examples: (a) Zhang, H.; Wu, X.; Wei, Y.; Zhu, C. Org. Lett. 2019, 21, 7568.
[11]
(b) White, L. V.; Schwartz, B. D.; Banwell, M. G.; Willis, A. C. J. Org. Chem. 2011, 76, 6250.
[11]
(c) Lim, Y.; Park, Y.-S.; Kang, Y.; Jang, D. Y.; Kim, J. H.; Kim, J.-J.; Sellinger, A.; Yoon, D. J. Am. Chem. Soc. 2011, 133, 1375.
[11]
(d) Yanagisawa, A.; Nishimura, K.; Ando, K.; Nezu, T.; Maki, A.; Kato, S.; Tamaki, W.; Imai, E.; Mohri, S.-I. Org. Process Res. Dev. 2010, 14, 1182.
[11]
(e) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed., 2005, 44, 4442.
[12]
For selected reviews and examples, see: (a) Dong, X.; Hou, Y.; Meng, F.; Liu, H.; Liu, H. Chin. J. Org. Chem. 2017, 37, 1088. (in Chinese)
[12]
(董旭, 侯永正, 孟凡威, 刘洪波, 刘会, 有机化学, 2017, 37, 1088.)
[12]
(b) Walker, B. R.; Sevov, C. S. ACS Catal. 2019, 9, 7197.
[12]
(c) Ehle, A. R.; Zhou, Q.; Watson, M. P. Org. Lett. 2012, 14, 1202.
[12]
(d) Gøgsig, T. M.; Kleimark, J.; Nilsson Lill, S. O.; Korsager, S.; Lindhardt, A. T.; Norrby, P.-O.; Skrydstrup, T. J. Am. Chem. Soc. 2011, 134, 443.
[12]
(e) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
[12]
(f) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
[12]
(g) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
[13]
(a) Djakovitch, L.; Wagner, M.; Hartung, C. G.; Beller, M.; Koehler, K. J. Mol. Catal. A: Chem. 2004, 219, 121.
[13]
(b) Bräse, S.; Schroen, M. Angew. Chem. Int. Ed. 1999, 38, 1071.
[13]
(c) Hartung, C. G.; Köhler, K.; Beller, M. Org. Lett. 1999, 1, 709.
[14]
For selected reviews and examples: (a) Huang, X.; Teng, S.; Chi, Y. R.; Xu, W.; Pu, M.; Wu, Y.-D.; Zhou, J. S. Angew. Chem. Int. Ed. 2021, 60, 2828.
[14]
(b) Jiao, Z.; Shi, Q.; Zhou, J. S. Angew. Chem. Int. Ed. 2017, 56, 14567.
[14]
(c) Desrosiers, J.-N.; Wen, J.; Tcyrulnikov, S.; Biswas, S.; Qu, B.; Hie, L.; Kurouski, D.; Wu, L.; Grinberg, N.; Haddad, N.; Busacca, C. A.; Yee, N. K.; Song, J. J.; Garg, N. K.; Zhang, X.; Kozlowski, M. C.; Senanayake, C. H. Org. Lett. 2017, 19, 3338.
[14]
(d) Oliveira, C. C.; Pfaltz, A.; Correia, C. R. D. Angew. Chem. Int. Ed. 2015, 54, 14036.
[14]
(e) Hu, J.; Hirao, H.; Li, Y.; Zhou, J. Angew. Chem. Int. Ed. 2013, 52, 8676.
[14]
(f) Werner, E. W.; Mei, T.-S.; Burckle, A. J.; Sigman, M. S. Science 2012, 338, 1455.
[14]
(g) Mc Cartney, D.; Guiry, P. J. Chem. Soc. Rev. 2011, 40, 5122.
[14]
(h) Tietze, L. F.; Ila, H.; Bell, H. P. Chem. Rev. 2004, 104, 3453.
[14]
(i) Dounay, A. B.; Overman, L. E. Chem. Rev. 2003, 103, 2945.
[15]
(a) Zhou, J. S.; Huang, X.; Teng, S.; Chi, Y. R. Chem. Commun. 2021, 57, 3933.
[15]
(b) Wu, X.; Lu, Y.; Hirao, H.; Zhou, J. S. Chem.-Eur. J., 2013, 19, 6014.
[15]
(c) Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt, M. J. J. Am. Chem. Soc. 2012, 134, 10773.
[15]
(d) Artuso, E.; Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. Tetrahedron 2006, 62, 3146.
[16]
Quasdorf, K. W.; Antoft-Finch, A.; Liu, P.; Silberstein, A. L.; Komaromi, A.; Blackburn, T.; Ramgren, S. D.; Houk, K. N.; Snieckus, V.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 6352.
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