SIOC English
有机化学
高级检索

有机化学 >

0 251014

DOI: https://doi.org/10.6023/cjoc202507003

研究论文

炔基亚砜的分子内交叉偶联/[3,3]-硫鎓离子重排策略构建环烷并[c]呋喃

  • 郭闻涛 ,
  • 孟书玉 ,
  • 王全瑞
展开
  • 复旦大学化学系 上海 200438

收稿日期: 2025-07-02

  修回日期: 2025-08-24

  网络出版日期: 2025-10-15

基金资助

国家自然科学基金(No. 21971042)资助项目.

收起

Intramolecular Cross-Coupling/[3,3]-Sulfonium Rearrangement of Alkynyl Sulfoxides for the Construction of Cycloalkano[c]furans

  • Guo Wentao ,
  • Meng Shuyu ,
  • Wang Quanrui
Expand
  • aDepartment of Chemistry, Fudan University, Shanghai 200438

Received date: 2025-07-02

  Revised date: 2025-08-24

  Online published: 2025-10-15

Supported by

National Natural Science Foundation of China (No. 21971042).

Fold

摘要

报道了一种基于分子内串联重排反应的双环呋喃类化合物的合成策略。该串联反应由三氟化硼乙醚络合物催化的炔基硫醚与炔基亚砜的分子内交叉偶联引发,随后经历[3,3]-σ硫鎓离子重排及5-exo-dig环化反应,最终以中等产率以及100%原子经济性获得产物环烷并[c]呋喃。所得呋喃类化合物的合成应用价值已通过对产物中烷硫基和呋喃环的后修饰反应得到验证。

关键词： [3,3]-重排; 硫鎓离子; 杂环化; 环烷并[c]呋喃; 分子内反应

本文引用格式

郭闻涛 , 孟书玉 , 王全瑞 . 炔基亚砜的分子内交叉偶联/[3,3]-硫鎓离子重排策略构建环烷并[c]呋喃[J]. 有机化学, 0 : 251014 . DOI: 10.6023/cjoc202507003

Abstract

An intramolecular tandem rearrangement for the synthesis of bicyclic furans is reported. The reaction was initiated by an intramolecular cross-coupling of the built-in alkynyl sulfoxide and alkynyl sulfide motifs in the presence of BF3·Et2O, followed by a [3,3]-sigmatropic sulfonium rearrangement and 5-exo-dig cyclization, affording cycloalkano[c]furans as final products in moderate yields with 100% atom economy. The synthetic utility of the resulting furans has been demonstrated through late-stage diversification by utilizing the alkylthio groups or the furan rings.

Key words： [3,3]-rearrangement; sulfonium ion; heterocyclization; cycloalkano[c]furan; intramolecular reaction

参考文献

[1] (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.;Wong, H. N. C.Tetrahedron 1998, 54, 1955.
(b) Hou, X.-L.; Yang, Z.; Yeung, K.-S.; Wong, H. N. C. in Prog. Heterocycl. Chem., Vol. 21 (Eds.: G. W. Gribble, J. A. Joule), Elsevier, 2009, pp. 179-223.
[2] (a) Kohmoto, S.; Mcconnell, O. J.; Wright, A.; Cross, S.Chem. Lett. 1987, 16, 1687.
(b) Fotso, S.; Maskey, R. P.; Grün-Wollny, I.; Schulz, K.-P.; Munk, M.; Laatsch, H.J. Antibiot. 2003, 56, 931.
(c) Ataur Rahman, M.;Kim, N.-H.;Yang, H.;Huh, S.-O.Mol. Cell. Biochem. 2012, 369, 95.
[3] Chiang Y.-M.; Szewczyk E.; Davidson A. D.; Keller N.; Oakley B. R.; Wang C. C.J. Am. Chem. Soc. 2009, 131, 2965.
[4] (a) Andersen, N. G.; Parvez, M.; Keay, B. A.Org. Lett. 2000, 2, 2817.
(b) Tan, W.; Wu, X.-Y.; Shi, F.ChemCathem. 2024, 16, e202401022.
[5] Heravi M. M.;Zadsirjan, V. inAdvances in Heterocyclic Chemistry, Vol 117, Vol. 117(Eds.: E. F. V. Scriven, C. A. Ramsden), 2015, pp. 261-376.
[6] (a) Lu S.; Ong J.-Y.; Yang H.; Poh S. B.; Liew X.; Seow C. S. D.; Wong M. W.; Zhao, Y. J. Am. Chem. Soc.2019, 141, 17062.
(b) Wang J.-Y.; Gao C.-H.; Ma C.; Wu X.-Y.; Ni S.-F.; Tan W.; Shi, F. Angew. Chem. Int. Ed.2024, 63, e202316454.
(c) Jin L.; Shi, B. Chin. J. Org. Chem.2024, 44, 657 (in Chinese).
(金良, 史炳锋, 有机化学, 2024, 44, 657).
[7] Manna S. K.; Giri S.; Mondal S.; Sana R. N.; Samal A. K.; Mandal A.Chemistryselect 2023, 8, e202203150.
[8] (a) Bai, Y.; Tao, W.; Ren, J.; Wang, Z.Angew. Chem. Int. Ed. 2012, 17, 4188.
(b) Yamashita, K.; Yamamoto, Y.; Nishiyama, H.J. Am. Chem. Soc. 2012, 134, 7660.
[9] (a) Zhou, L.; Li, Z.; Zou, Y.; Wang, Q.; Sanhueza, I. A.; Schoenebeck, F.; Goeke, A.J. Am. Chem. Soc. 2012, 134, 20009.
(b) Zou, Y.; Ding, C.; Zhou, L.; Li, Z.; Wang, Q.; Schoenebeck, F.; Goeke, A.Angew. Chem. Int. Ed. 2012, 51, 5647.
(c) Meng, S.; Guo W.; Liu, J.; Zheng, J.; Wang, Q.Chemistryselect 2022, 7, e202202760.
[10] (a) Meng, S.; Wang, Y.; Liu, J.; Zheng, J.; Qian, X.; Wang Q.Org. Lett. 2022, 24, 757.
(b) Meng, S.; Guo, W.; Wang, Q.Chin. J. Org. Chem. 2024, 44, 2274.
[11] Kaldre D.; Klose I.; Maulide N.Science 2018, 361, 664.
[12] Schaumann E.Sulfur-Mediated Rearrangements II, Vol. 2, Springer-Verlag: Berlin Heidelberg, 2007, pp. 14-49.
[13] Pommainville A.; Campeau D.; Gagosz F.Angew. Chem. Int. Ed. 2022, 61, e202205963.
[14] Trost B. M.; Curran D. P.Tetrahedron Lett. 1981, 22, 1287.
[15] Yamamoto Y.; Gridnev I. D.; Patil N. T.; Jin T.Chem. Commun. 2009, 5075.
[16] (a) Illuminati, G.; Mandolini, L.Acc. Chem. Res. 1981, 14, 95.
(b) Galli, C.; Mandolini, L.Eur. J. Org. Chem. 2000, 3117.
(c) Reyes R. L.; Iwai T.; Sawamura M. Chem. Rev.2021, 121, 8926.
[17] Baralle A.; Otsuka S.; Guérin V.; Murakami K.; Yorimitsu H.; Osuka A.Synlett 2015, 26, 327.
[18] Kappe C. O.; Murphree S. S.; Padwa A.Tetrahedron 1997, 53, 14179.
[19] (a) Sarkar, T. K.; Panda, N.; Basak, S.J. Org. Chem. 2003, 68, 6919.
(b) Haut, F.-L.; Habiger, C.; Wein, L. A.; Wurst, K.; Podewitz, M.; Magauer, T.J. Am. Chem. Soc. 2021, 143, 1216.
Options
文章导航

/

〈 〉