SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

0 202604029 - 202604029

DOI: https://doi.org/10.6023/cjoc202604029

ARTICLE

Mn-Catalyzed Radical Brook Rearrangement/Alkenylation of α-Silyl Cyclobutanols

  • Xiang Li ,
  • Yizhi Zhang ,
  • Gang Zhou ,
  • Xiaolei Liu ,
  • Xiao Shen
Expand
  • aInstitute for Smart Material & Engineering, University of Jinan, Jinan, 250022;
    bInstitute for Advanced Studies, Wuhan University, Wuhan, 430072;
    cEngineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan, 430072

Received date: 2026-04-21

  Revised date: 2026-05-13

  Online published: 2026-05-27

Supported by

National Key Research and Development Program of China (2022YFA1506100) and the National Natural Science Foundation of China (22531010, 22471201, 21901191)

Fold

Abstract

A manganese-catalyzed radical Brook rearrangement/alkenylation cascade reaction of α-silyl cyclobutanols with 1,1-diarylalkenes is reported, enabling the synthesis of alkenylated cyclobutyl silyl ethers. This reaction exhibits excellent functional group tolerance and a broad substrate scope. Furthermore, scale-up experiments and synthetic applications demonstrate the potential utility of this strategy in organic synthesis.

Key words： manganese catalysis; alkenylation; radical Brook rearrangement; cyclobutanols

Cite this article

Xiang Li , Yizhi Zhang , Gang Zhou , Xiaolei Liu , Xiao Shen . Mn-Catalyzed Radical Brook Rearrangement/Alkenylation of α-Silyl Cyclobutanols[J]. Chinese Journal of Organic Chemistry, 0 : 202604029 -202604029 . DOI: 10.6023/cjoc202604029

References

[1] Carreira E. M.; Fessard, T. C. Chem. Rev.2014, 114, 8257-8322.
[2] Marek, I. Chem. Rev.2021, 121, 264-299.
[3] van der Kolk, M. R.; Janssen M. A. C. H.; Rutjes F. P. J. T.; Blanco-Ania D. ChemMedChem.2022, 17, No. e202200020.
[4] Taylor R. D.;MacCoss, M.; Lawson, A. D. G.J. Med. Chem. 2014, 57, 5845-5859.
[5] Li Y.; Pattenden, G. Nat. Prod. Rep.2011, 28, 1269-1310.
[6] Natho P.; Allen L. A. T.; Parsons, P. J. Tetrahedron Lett.2020, 61, 151695-151704.
[7] Wu X.; Zhu C. Chem. Rec.2018, 18, 587-598.
[8] Song Z. L.; Fan C. A.; Tu, Y. Q. Chem. Rev.2011, 111, 7523-7556.
[9] Ren R.; Wu Z.; Xu Y.; Zhu, C. Angew. Chem. Int. Ed.2016, 55, 2866-2869.
[10] Ren R.; Zhao H.; Huan L.; Zhu, C. Angew. Chem. Int. Ed.2015, 54, 12692-12696.
[11] Kwon S. J.; Kim, D. Y. Org. Lett.2016, 18, 4562-4565.
[12] Zeng H.; Pan P.; Chen J.; Gong H.; Li C.-J.Eur. J. Org. Chem. 2017, 1070-1073.
[13] Liu M.; Huang H.; Chen, Y. Chin. J. Chem.2018, 36, 1209-1212.
[14] Yayla H. G.; Wang H.; Tarantino K. T.; Orbe H. S.; Knowles, R. R. J. Am. Chem. Soc.2016, 138, 10794-10797.
[15] Ren R.; Wu Z.; Zhu C. Chem. Commun.2016, 52, 8160-8163.
[16] Seiser T.; Cramer, N. Angew. Chem. Int. Ed.2008, 47, 9294-9297.
[17] Hall, H. K. Jr.; Smith C. D.; Blanchard, E. P. Jr.; Cherkofsky S. C.; Sieja, J. B. J. Am. Chem. Soc.1971, 93, 121-130.
[18] Pritzkow W.; Suprun V. Y.; Voerckel, V. J. Prakt. Chem.1990, 332, 381-386.
[19] Zhang Y.; Zhang Y.; Shen X. Chem. Catal.2021, 1, 423-436.
[20] Chen X.; Gong X.; Li Z.; Zhou G.; Zhu Z.; Zhang W.; Liu S.; Shen X. Nat. Commun.2020, 11, 2756.
[21] Chen X.; Zhu Z.; Liu S.; Chen Y.-H.; Shen, X. Chin. Chem. Lett.2022, 33, 2391-2396.
[22] Deng S.; Peng C.; Niu Y.; Xu Y.; Zhang Y.; Chen X.; Wang H.; Liu S.; Shen, X. Acta Chim. Sin.2024, 82, 119-125.
[23] Gilman H.; Wu, T. C. J. Am. Chem. Soc.1953, 75, 2935-2936.
[24] Brook, A. G. J. Am. Chem. Soc.1958, 80, 1886-1889.
[25] Fleming I.; Barbero A.; Walter D.Chem. Rev. 1997, 97, 2063-2192.
[26] Smith M. A.; Willeford, B. R., Jr. J. Am. Chem. Soc.1954, 76, 2502.
[27] Gilman H.; Lichtenwalter, G. D. J. Am. Chem. Soc.1958, 80, 2680-2682.
[28] Brook, A. G. Acc. Chem. Res.1974, 7, 77-84.
[29] Brook A. G.; Duff, J. M. J. Am. Chem. Soc.1967, 89, 454-455.
[30] Bourque R. A.; Davis P. D.; Dalton, J. C. J. Am. Chem. Soc.1981, 103 , 697-699.
[31] Tsai Y.-M.; Cherng C.-D. Tetrahedron Lett.1991, 32, 3515-3518.
[32] Cunico, R. F. Tetrahedron Lett.2001, 42, 2931-2932.
[33] Deng Y.; Liu Q.; Smith, A. B., III. J. Am. Chem. Soc.2017, 139, 9487-9490.
[34] Le C.; Chen T. Q.; Liang T.; Zhang P.; MacMillan, D. W. C. Science2018, 360, 1010-1014.
[35] Ye J.-H.; Quach L.; Paulisch T.; Glorius, F. J. Am. Chem. Soc.2019, 141, 16227-16231.
[36] Ito K.; Tamashima H.; Iwasawa N.; Kusama, H. J. Am. Chem. Soc.2011, 133, 3716-3719.
[37] Stuckhardt C.; Wissing M.; Studer, A. Angew. Chem. Int. Ed.2021, 60, 18605-18611.
[38] Zhang Y.; Chen J.-J.; Huang, H.-M. Angew. Chem. Int. Ed.2022, 61, e202205671.
[39] Qin T.; Xu C.; Zhang G.; Zhang,Q.Org. Chem. Front., 2023,10, 1981-1987.
[40] Zhou P.; Ding L.; Liu Y.; Song H.; Wang Q. Org. Lett.2024, 26, 7094-7099.
[41] Liu X.-B.; Bilal M.; Zuo J.; Yu Y.-X.; Wu Y.-J.; Shen B.; Shen P.-H.; Xu H.-J.; Liang Y.-F.Chem. Sci. 2026, DOI: 10.1039/D6SC00986G.
[42] Wang A.-L.; Yao Y.-F.; Zhang X.-G.; Xu P.-F. Org. Lett.2026, 28, 1550-1560.
[43] Chen L.-N.; Chen D.-N.; Qin L.-L.; Luo D.-J.; Lv Y.; Tang W. K.; Tang H.-T.; Wu H.; Yang H.; Xia P.-J.Org. Lett. 2026, DOI: 10.1021/acs.orglett.6c00985.
[44] Zhang Y.; Zhang Y.; Guo Y.; Liu S.; Shen X. Chem Catal.2022, 2, 1380-1393.
[45] Zhang Y.; Zhou G.; Liu S.; Shen X.Chem. Soc. Rev. 2025, 54, 1870-1904.
[46] Yao Y.; Zhou G.; Liu S.; Qi X.; He X.; Shen X. Chin. J. Chem.2026, 44, 1624-1630.
[47] Jin P.; He X.; Liu S.; Qi X.; Shen X. CCS Chem.2026, 8, 1267-1275.
[48] Zhou G.; Yao Y.; He X.; Zhang W.; Liu S., Shen X. Chem.2026, 12, 102721.
[49] Shen, X. Acc. Chem. Res.2025, 58, 1519-1533
[50] Zhang W.; Chen S.; Zhang Y.; Liu S.; Shen X.Angew. Chem. Int. Ed. 2025, 64, e202422020.
[51] Liu Y.; Zhu Z.; Zhang Y.; Zhang Y.; Liu S.; Shen X. Org. Lett.2024, 26, 5911-5916.
[52] Zhou G.; Guo Z.; Liu S.; Shen, X. J. Am. Chem. Soc.2024, 146, 4026-4035.
[53] Zhou G.; Guo Z.; Shen, X. Angew. Chem. Int. Ed.2023, 62, e202217189.
Options
Outlines

/

〈 〉