SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 1: 331 - 342

DOI: https://doi.org/10.6023/cjoc202405011

ARTICLES

Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds

  • Fan Yang ,
  • Xiaomeng Fan ,
  • Xuejing Yao ,
  • Ruijie Mi ,
  • Songjie Yu ,
  • Xingwei Li ,
  • Jian Xiao
Expand
  • a College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, Shandong 266109
    b Institute of Frontier Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Qingdao, Shandong 266237
†These authors contributed equally to this work.
*E-mail: ;
;
;

Received date: 2024-05-10

  Revised date: 2024-06-16

  Online published: 2024-07-18

Supported by

Taishan Scholars Construction Projects of Shandong Province(tsqn201909131)

Fold

Abstract

The Rh(III)-catalyzed C—H functionalization of sulfoxonium ylides and successively annulation with two classes of cyclic diazo compounds has been realized, affording structurally diverse fused-ring or spirocyclic compounds under redox- neutral conditions. The reaction proceeds via successive chelation-assisted C—H activation, carbene insertion, and intra- molecular [3 ＋ 3]/[4 ＋ 1] annulation processes.

Key words： rhodium catalysis; sulfoxonium ylide; C—H activation; diazo compound; annulation

Cite this article

Fan Yang , Xiaomeng Fan , Xuejing Yao , Ruijie Mi , Songjie Yu , Xingwei Li , Jian Xiao . Rhodium(III)-Catalyzed Annulative Coupling between Sulfoxonium Ylides and Diazo Compounds[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 331 -342 . DOI: 10.6023/cjoc202405011

References

[1]
For selected reviews, see: (a) Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976.
[1]
(b) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068.
[1]
(c) Ackermann, L. Chem. Rev. 2011, 111, 1315.
[1]
(d) He, J.; Wasa, M.; Chan, K. S. L.; Shao, Q.; Yu, J. Q. Chem. Rev. 2017, 117, 8754.
[1]
(e) Yang, Y. D.; Lan, J. B.; You, J. S. Chem. Rev. 2017, 117, 8787.
[1]
(f) Dong, Z.; Ren, Z.; Thompson, S. J.; Xu, Y.; Dong, G. B. Chem. Rev. 2017, 117, 9333.
[1]
(g) Hummel, J. R.; Boerth, J. A.; Ellman, J. A. Chem. Rev. 2017, 117, 9163.
[1]
(h) Gandeepan, P.; Müller, T.; Zell, D.; Cera, G.; Warratz, S.; Ackermann, L. Chem. Rev. 2019, 119, 2192.
[1]
(i) Yu, X.; Zhang, Z.; Niu, J. L.; Shi, B. F. Org. Chem. Front. 2022, 9, 1458.
[1]
(j) Lu, M. Z.; Goh, J.; Maraswami, M.; Jia, Z.; Tian, J. S.; Loh, T. P. Chem. Rev. 2022, 122, 17479.
[1]
(k) Brandes, D. S.; Ellman, J. A. Chem. Soc. Rev. 2022, 51, 6738.
[1]
(l) Yu, I. F.; Wilson, J. W.; Hartwig, J. F. Chem. Rev. 2023, 123, 11619.
[2]
(a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
[2]
(b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
[2]
(c) Shi, Z. Z.; Koester, D. C.; Boultadakis-Arapinis, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 12204.
[2]
(d) Piou, T.; Rovis, T. Acc. Chem. Res. 2018, 51, 170.
[2]
(e) Zeng, Z. Y.; Gao, H.; Zhou, Z.; Yi, W. ACS Catal. 2022, 12, 14754.
[2]
(f) Liu, C. X.; Yin, S. Y.; Zhao, F.; Yang, H.; Feng, Z.; Gu, Q.; You, S. L. Chem. Rev. 2023, 123, 10079.
[3]
(a) Li, A. H.; Dai, L. X.; Aggarwal, V. K. Chem. Rev. 1997, 97, 2341.
[3]
(b) Aggarwal, V. K.; Winn, C. L. Acc. Chem. Res. 2004, 37, 611.
[3]
(c) Lu, L. Q.; Li, T.; Wang, Q.; Xiao, W. Chem. Soc. Rev. 2017, 46, 4135.
[3]
(d) Zhang, J.; Zhang, C.; Zheng, Z.; Zhou, P.; Liu, W. Chin. J. Org. Chem. 2022, 42, 2745 (in Chinese).
[3]
(张建涛, 张聪, 郑梓栋, 周鹏, 刘卫兵, 有机化学, 2022, 42, 2745.)
[4]
For reviews, see: (a) Kumar, A.; Sherikar, M. S.; Hanchate, V.; Prabhu, K. R. Tetrahedron 2021, 101, 132478.
[4]
(b) Bhorali, P.; Sultana, S.; Gogoi, S. Asian J. Org. Chem. 2022, 11, e202100754.
[4]
(c) Singh, A.; Kumar, S.; Volla, C. M. R. Org. Biomol. Chem. 2023, 21, 879.
[4]
(d) Hong, C.; Jiang, X.; Yu, S.; Liu, Z.; Zhang, Y. Chin. J. Org. Chem. 2021, 41, 888 (in Chinese).
[4]
(洪超, 蒋希程, 于书玲, 刘占祥, 张玉红, 有机化学, 2021, 41, 888.)
[5]
(a) Barday, M.; Janot, C.; Halcovitch, N. R.; Muir, J.; Aïssa, C. Angew. Chem., Int. Ed. 2017, 56, 13117.
[5]
(b) Xu, Y. W.; Zhou, X. K.; Zheng, G. F.; Li, X. W. Org. Lett. 2017, 19, 5256.
[6]
(a) Xu, Y. W.; Yang, X. F.; Zhou, X. K.; Kong, L. H.; Li, X. W. Org. Lett. 2017, 19, 4307.
[6]
(b) Yu, Y. Q.; Wu, Q. L.; Liu, D.; Yu, L.; Tan, Z.; Zhu, G. G. Org. Chem. Front. 2019, 6, 3868.
[6]
(c) Hanchate, V.; Kumar, A.; Prabhu, K. R. Org. Lett. 2019, 21, 8424.
[6]
(d) Xie, W.; Lin, B.; Jian, X.; Lin, Q.; Shi, J. Synlett 2020, 1482.
[6]
(e) Liu, R. X.; Wei, Y.; Shi, M. ChemCatChem 2020, 12, 5903.
[6]
(f) Xie, W. C.; Jian, X. Y.; Zhang, L. Y.; Jin, K. X.; Shi, J. J.; Zhu, F. Org. Biomol. Chem. 2021, 19, 1498.
[6]
(g) Wang, P. Y.; Huang, Y. L.; Jing, J. R.; Wang, F.; Li, X. W. Org. Lett. 2022, 24, 2531.
[7]
(a) Wang, P. Y.; Xu, Y. W.; Sun, J. Q.; Li, X. W. Org. Lett. 2019, 21, 8459.
[7]
(b) Lou, J.; Wang, Q. N.; Zhou, Y.-G.; Yu, Z. K. Org. Lett. 2019, 21, 9217.
[8]
(a) Kommagalla, Y.; Ando, S.; Chatani, N. Org. Lett. 2020, 22, 1375.
[8]
(b) Hanchate, V.; Devarajappa, R.; Prabhu, K. R. Org. Lett. 2020, 22, 2878.
[9]
Dong, Y.; Yu, J.-T.; Sun, S.; Cheng, J. Chem. Commun. 2020, 56, 6688.
[10]
(a) Yu, Y. Q.; Xia, Z.; Wu, Q. L.; Liu, D.; Yu, L.; Xiao, Y. J.; Tan, Z.; Deng, W.; Zhu, G. G. Chin. Chem. Lett. 2021, 32, 1263.
[10]
(b) Yin, C. L.; Li, L. H.; Yu, C. M. Org. Biomol. Chem. 2022, 20, 1112.
[11]
For representative individual reports, see: (a) Chan, W.-W.; Lo, S.-F.; Zhou, Z. Y.; Yu, W.-Y. J. Am. Chem. Soc. 2012, 134, 13565.
[11]
(b) Yu, X. Z.; Yu, S. J.; Xiao, J.; Wan, B. S.; Li, X. W. J. Org. Chem. 2013, 78, 5444.
[11]
(c) Hu, F. D.; Xia, Y.; Ye, F.; Liu, Z. X.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 1364.
[11]
(d) Liang, Y. J.; Yu, K.; Li, B.; Xu, S. S.; Song, H. B.; Wang, B. Q. Chem. Commun. 2014, 50, 6130.
[11]
(e) Ford, A.; Miel, H.; Ring, A.; Slattery, C. N.; Maguire, A. R.; McKervey, M. A. Chem. Rev. 2015, 115, 9981.
[11]
(f) Yu, S. J.; Liu, S.; Lan, Y.; Wan, B. S.; Li, X. W. J. Am. Chem. Soc. 2015, 137, 1623.
[11]
(g) Wu, J. Q.; Yang, Z.; Zhang, S.-S.; Jiang, C. Y.; Li, Q.; Huang, Z. S.; Wang, H. ACS Catal. 2015, 5, 6453.
[11]
(h) Yang, Y.; Wang, X.; Li, Y. C.; Zhou, B. Angew. Chem., Int. Ed. 2015, 54, 15400.
[11]
(i) Dateer, R. B.; Chang, S. Org. Lett. 2016, 18, 68.
[11]
(j) Li, J.; Tang, M. Y.; Zang, L.; Zhang, X. L.; Zhang, Z.; Ackermann, L. Org. Lett. 2016, 18, 2742.
[11]
For selected reviews, see: (k) Xia, Y.; Qiu, D.; Wang, J. B. Chem. Rev. 2017, 117, 13810.
[11]
(l) Wang, M. M.; Kong, L. H.; Wu, Q. Y.; Li, X. W. Org. Lett. 2018, 20, 4597.
[11]
(m) Xiang, Y. Y.; Wang, C.; Ding, Q. P.; Peng, Y. Y. Adv. Synth. Catal. 2019, 361, 919.
[11]
(n) He, Y.; Huang, Z. L.; Wu, K. K.; Ma, J.; Zhou, Y.-G.; Yu, Z. K. Chem. Soc. Rev. 2022, 51, 2759.
[11]
(o) Li, S.; Zhou, L. Chin. J. Org. Chem. 2022, 42, 3944 (in Chinese).
[11]
(李森, 周磊, 有机化学, 2022, 42, 3944.)
[11]
(p) Xie, Y.; Xuan, J. Chin. J. Org. Chem. 2022, 42, 4247 (in Chinese).
[11]
(谢阳, 宣俊, 有机化学, 2022, 42, 4247.)
[12]
(a) Zhang, S. S.; Jiang, C. Y.; Wu, J. Q.; Liu, X. G.; Li, Q.; Huang, Z. S.; Li, D.; Wang, H. Chem. Commun. 2015, 51, 10240.
[12]
(b) Jia, Z. J.; Merten, C.; Gontla, R.; Daniliuc, C. G.; Antonchick, A. P.; Waldmann, H. Angew. Chem., Int. Ed. 2017, 56, 2429.
[12]
(c) Jang, Y. S.; Wozniak, L.; Pedroni, J.; Cramer, N. Angew. Chem., Int. Ed. 2018, 57, 12901.
[12]
(d) Zou, Y.; Wang, P. Y.; Kong, L. H.; Li, X. W. Org. Lett. 2022, 24, 3189.
[13]
(a) Han, X.; Kong, L. H.; Feng, J. M.; Li, X. W. Chem. Commun. 2020, 56, 5528.
[13]
(b) Kong, L. H.; Han, X.; Liu, S.; Zou, Y.; Lan, Y.; Li, X. W. Angew. Chem., Int. Ed. 2020, 59, 7188.
[14]
Chen, R. J.; Cui, S. L. Org. Lett. 2017, 19, 4002.
[15]
Giri, C. K.; Mondal, S.; Baidya, M. Org. Chem. Front. 2023, 10, 5856.
[16]
(a) Chen, X.; Wang, M. H.; Zhang, X. Y.; Fan, X. S. Org. Lett. 2019, 21, 2541.
[16]
(b) Song, X. H.; Han, X.; Zhang, R.; Liu, H.; Wang, J. Molecules 2019, 24, 1884.
[17]
Sun, L. C.; Liu, B. X.; Zhao, Y. L.; Chang, J. B.; Kong, L. H.; Fen Wang, F.; Deng, W. Q.; Li, X. W. Chem. Commun. 2021, 57, 8268.
Options
Outlines

/

〈 〉