REVIEW

Progress in the Synthesis of 1,3-Disubstituted Ferrocene

  • Hu Ruixin ,
  • Huang Xiao ,
  • Jiao Chengkang ,
  • Zhou Qianghui ,
  • Cheng Hong-Gang
Expand
  • College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072
#These authors contributed equally to this work.

Received date: 2026-07-16

  Revised date: 2026-08-02

  Online published: 2026-08-28

Supported by

National Natural Science Foundation of China (Nos. 22325106 and 22471204) and Natural Science Foundation of Jiangsu Province (no. BK20210119).

Abstract

Ferrocene is a kind of functional molecule which is widely used in catalysis, medicine, materials and other fields. Compared with the extensive synthesis of 1,2-disubstituted ferrocenes, the synthesis of 1,3-disubstituted ferrocenes, especially the planar-chiral 1,3-disubstituted ferrocenes, is relatively limited. This review summarizes recent progress on the development of novel methods to synthesize 1,3-disubstituted ferrocenes and their planar-chiral derivatives. In addition, the application of these synthetic methods in the preparation of planar-chiral functional materials, 1,3-disubstituted planar-chiral ferrocene ligands as well as their utilization in catalytic asymmetric reactions are also described.

Cite this article

Hu Ruixin , Huang Xiao , Jiao Chengkang , Zhou Qianghui , Cheng Hong-Gang . Progress in the Synthesis of 1,3-Disubstituted Ferrocene[J]. Chinese Journal of Organic Chemistry, 0 : 0 . DOI: 10.6023/cjoc202607018

References

[1] Kealy T. J.; Pauson P. L. Nature1951, 168, 1039.
[2] Gómez Arrayás R.; Adrio J.; Carretero, J. C. Angew. Chem. Int. Ed.2006, 45, 7674.
[3] Cunningham L.; Benson A.; Guiry, P. J. Org. Biomol. Chem.2020, 18, 9329.
[4] Patra M.; Gasser, G. Nat. Rev. Chem.2017, 1, 0066.
[5] Alba A. N. R.; Rios R. Molecules2009, 14, 4747.
[6] Lambusta D.; Nicolosi G.; Patti A.; Piattelli M. Tetrahedron Lett.1996, 37, 127.
[7] Patti A.; Lambusta D.; Piattelli M.; Nicolosi G.; Mcardle P.; Cunningham D.; Walsh M. Tetrahedron1997, 53, 1361.
[8] Battelle L. F.; Bau R.; Gokel G. W.; Oyakawa R. T.; Ugi, I. K. J. Am. Chem. Soc.1973, 95, 482.
[9] Richards C. J.; Damalidis T.; Hibbs D. E.; Hursthouse M. B.Synlett 1995, 74.
[10] Bolm C.; Kesselgruber M.; Raabe G. Organometallics2002, 21, 707.
[11] Tsukazaki M.; Tinkl M.; Roglans A.; Chapell B. J.; Taylor N. J.; Snieckus, V. J. Am. Chem. Soc.1996, 118, 685.
[12] Genet C.; Canipa S. J.; O'brien P.; Taylor, S. J. Am. Chem. Soc.2006, 128, 9336.
[13] Laufer R. S.; Veith U.; Taylor N. J.; Snieckus V.Org. Lett. 2000, 2, 629.
[14] (a) Gao D.-W.; Shi Y.-C.; Gu Q.; Zhao Z.-L.; You, S.-L. J. Am. Chem. Soc.2013, 135, 86.
(b) Pi C.; Li Y.; Cui X.-L.; Zhang H.; Han Y.-B.; Wu Y.-J. Chem. Sci.2013, 4, 2675.
(c) Pi C.; Cui X.-L.; Liu X.-Y.; Guo M. X.; Zhang H.-Y.; Wu Y.-J. Org. Lett.2014, 16, 5164.
(d) Liu, C.-X.; Zhao, F.; Gu, Q.; You, S.-L.ACS Cent. Sci. 2023, 9, 2036.
(e) Lv X.; Wang M.; Zhao Y.; Shi, Z. J. Am. Chem. Soc.2024, 146, 3483.
(f) Mou Q.; Zhao R.; Niu R.; Fukagawa S.; Shigeno T.; Yoshino T.; Matsunaga S.; Sun, B. Org. Chem. Front.2021, 8, 6923.
(g) Zou X.; Li Y.; Ke Z.; Xu S. ACS Catal.2022, 12, 1830.
(h) Liu L.; Song H.; Liu Y.-H.; Wu L.-S.; Shi B.-F. ACS Catal.2020, 10, 7117.
(i) Huang F.-R.; Zhang P.; Yao Q.-J.; Shi B.-F. CCS Chem.2024, 6, 2783.
(j) Shibata T.; Shizuno T.; Sasaki T. Chem. Commun.2015, 51, 7802.
[15] Caniparoli U.; Escofet I.; Echavarren A. M.ACS Catal. 2022, 12, 3317.
[16] Muraoka T.; Kinbara K.; Kobayashi Y.; Aida, T. J. Am. Chem. Soc.2003, 125, 5612.
[17] Muraoka T.; Kinbara K.; Aida T. Nature2006, 440, 512.
[18] Chuard T.; Cowling S. J.; Fernandez-Ciurleo, M.; Jauslin, I.; Goodby. J. W.; Deschenaux, R.Chem. Commun. 2000, 2109.
[19] Brettar J.; Bürgi T.; Donnio B.; Guillon D.; Klappert R.; Scharf T.; Deschenaux, R. Adv. Funct. Mater.2006, 16, 260.
[20] Santamaría J.; García-Martínez P.; López, L. Asian J. Org. Chem.2024, 13, e202400301.
[21] Friedel C.; Crafts, J. M. Compt. Rend.1877, 84, 1392.
[22] Friedel C.; Crafts, J. M. Bull. Soc. Chim. Fr.1877, 27, 530.
[23] Leigh T.J. Chem. Soc. 1964, 3294.
[24] Nesmeyanov A. N.; Leonova E. V.; Kochetkova N. S.; Makarovskaya, A. G. J. Organomet. Chem.1975, 96, 275.
[25] Hisatome M.; Tachikawa O.; Sasho M.; Yamakawa, K. J. Organomet. Chem.1981, 217, C17.
[26] Blckert P.; Hildebrandt B.; Hafner K. Organometallics1984, 3, 653.
[27] Koridze A. A.; Sheloumov A. M.; Kuklin S. A.; Lagunova V. Y.; Petukhova, I. Russ. Chem. Bull. Int. Ed.2002, 51, 988.
[28] Bonini B. F.; Capito E.; Comes-Franchini M.; Fochi M.; Ricci A. Arkivoe,2006, vi, 85.
[29] Lee S.-G.; Lee H.-K.; Lee S. S.; Chung Y. K.Organometallics 1997, 16, 304.
[30] Broussier R.; Bentabet E.; Mellet P.; Blacque O.; Boyer P.; Kubicki M.; Gautheron, B. J. Organomet. Chem.2000, 598, 365.
[31] Pichon C.; Odell B.; Brown J. M.Chem. Commun.2004, 598.
[32] Masson G.; Lough A. J.; Manners I. Macromolecules 2008, 41, 539.
[33] Slocum D. W.; Koonsvitsky B. P.; Ernst, C. R. J. Organomet. Chem.1972, 38, 125.
[34] Slocum D. W.; Marchal R. L.; Jones W. E.Chem. Commun.1974, 967.
[35] Zirakzadeh A.; Hrlein A.; Grob M. A.; Mereiter K.; Wang Y.; Weissensteiner W. Organometallics2015, 34, 3820.
[36] Bulter I. R.; Woldt B.; Oh M.-Z.; Williams D. J.Inorg. Chem. Commun. 2006, 9, 1255.
[37] Tazi M.; Erb W.; Halauko Y. S.; Ivashkevich O. A.; Mongin F. Organometallics2017, 36, 4770.
[38] Ishiyama T.; Takagi J.; Hartwig J. F.; Miyaura, N. Angew. Chem. Int. Ed.2002, 41, 3056.
[39] Datta A.; Köllhofer A.; Plenio H.Chem. Commun. 2004, 1508.
[40] Zheng H.; Liu C.-H.; Wang X.-Y.; Liu Y.; Chen Q.Adv. Sci. 2023, 10, 2304672.
[41] Gupta P.; Madhavan S.; Kapur, M. Angew. Chem. Int. Ed.2023, 62, e202305278.
[42] Gupta P.; Patel B.; Waske S.; Madhavan S.; Kapur M. Chem. Commun.2026, 62, 6364.
[43] Westman L.; Rinehart J.; Kenneth, L. Acta Chem. Scand.1962, 16, 1199.
[44] Izumi T.; Hino T.Technol. Biotechnol. 1992, 55, 325.
[45] D’Antona N.; Lambusta D.; Morrone R.; Nicolosi G.; Secundo, F. Tetrahedron: Asymmetry 2004, 15,3835.
[46] Marquarding D.; Klusacek H.; Gokel G.; Hoffmann P.; Ugi, I. J. Am. Chem. Soc.1970, 92, 5389.
[47] Steurer M.; Tiedl K.; Wang Y.; Weissensteiner W.Chem. Commun.2005, 4929.
[48] Steurer M.; Wang Y.; Mereiter K.; Weissensteiner W. Organometallics2007, 26, 3850.
[49] Ferber B.; Top S.; Welter R.; Jaouen G.Chem. Eur. J. 2006, 12, 2081.
[50] Rebière F.; Riant O.; Ricard L.; Kagan, H. B. Angew. Chem. Int. Ed.1993, 32, 568.
[51] Ferber B.; Kagan H. B.Adv. Synth. Catal. 2007, 349, 493.
[52] Sasamori T.; Sakagami M.; Niwa M.; Sakai H.; Furukawa Y.; Tokitoh N. Chem. Commun.2012, 48, 8562.
[53] (a) Giri R.; Shi B.-F.; Engle K. M.; Maugel, N. Yu, J.-Q. Chem. Soc. Rev.2009, 38, 3242.
(b) Wencel-Delord J.; Colobert, F. Chem. Eur. J.2013, 19, 14010.
(c) Zheng C.; You S.-L. RSC Adv.2014, 4, 6173.
(d) Ye B.; Cramer, N. Acc. Chem. Res.2014, 48, 1308.
(e) Newton C. G.; Wang S.-G.; Oliveira, C C.; Cramer N. Chem. Rev.2017, 117, 8908.
(f) Saint-Denis T. G.; Zhu, R Y.; Chen G.; Wu Q.-F.; Yu J.-Q. Science2018, 359, eaao4798.
[54] Liu C.-X.; Zhao F.; Feng Z.; Wang Q.; Gu Q.; You S.-L. Nat. Synth.2023, 2, 49.
[55] Zhou L.; Cheng H.-G.; Li L.; Yu J.-Q.; Zhou Q. Nat. Chem.2023, 15, 815.
[56] Gupta P.; Tiwari P.; Madhavan S.; Kapur M. ACS Catal. 2024, 14, 17460.
Outlines

/