Direct C–O Bond Activation Mediated by AcOH: A New Metal-Free Way for α-Functionalization of Ferrocene Alcohols
Ran Jiang A , Xue-Qiang Chu A , Xiao-Ping Xu A , Bin Wu A and Shun-Jun Ji A B
+ Author Affiliations
- Author Affiliations
A Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. China.
B Corresponding author. Email: chemjsj@suda.edu.cn
Australian Journal of Chemistry 64(11) 1530-1537 https://doi.org/10.1071/CH11167
Submitted: 28 April 2011 Accepted: 10 August 2011 Published: 16 November 2011
Abstract
α-functionalization of ferrocenyl alcohols by direct C–O bond activation by indoles, active methylene compounds, electron-rich arenes, anilines, alcohols, and thiols in acetic acid is described. This protocol provides a relatively green and efficient combinatorial access to ferrocene derivatives in a metal-free manner.
References
[1] (a) K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, Angew. Chem. Int. Ed. 2006, 45, 2605.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XjvVCmt70%3D&md5=9b7c2270ec28c936765ef26c4da5dc14CAS |
(b) P.-N. Liu, Z.-Y. Zhou, C.-P. Lau, Chem. – Eur. J. 2007, 13, 8610.
| Crossref | GoogleScholarGoogle Scholar |
(c) R. Sanz, D. Miguel, A. Martínez, J. M. Álvarez-Gutiérrez, F. Rodríguez, Org. Lett. 2007, 9, 2027.
| Crossref | GoogleScholarGoogle Scholar |
(d) M. Yoshimatsu, T. Otani, S. Matsuda, T. Yamamoto, A. Sawa, Org. Lett. 2008, 10, 4251.
| Crossref | GoogleScholarGoogle Scholar |
(e) Z. Zhan, W. Wang, R. Yang, J. Yu, J. Li, H. Liu, Chem. Commun. 2006, 3352,
| Crossref | GoogleScholarGoogle Scholar |
(f) Y. Nishibayashi, A. Shinoda, Y. Miyake, H. Matsuzawa, M. Sato, Angew. Chem. Int. Ed. 2006, 45, 4835.
| Crossref | GoogleScholarGoogle Scholar |
(g) T. Saito, Y. Nishimoto, M. Yasuda, A. Baba, J. Org. Chem. 2006, 71, 8516.
| Crossref | GoogleScholarGoogle Scholar |
(h) M. Yasuda, T. Somyo, A. Baba, Angew. Chem. Int. Ed. 2006, 45, 793.
| Crossref | GoogleScholarGoogle Scholar |
(i) M. Rueping, B. J. Nachtsheim, A. Kuenkel, Org. Lett. 2007, 9, 825.
| Crossref | GoogleScholarGoogle Scholar |
(j) M. Noji, Y. Konno, K. Ishii, J. Org. Chem. 2007, 72, 5161.
| Crossref | GoogleScholarGoogle Scholar |
(k) K. Manabe, S. Limura, X.-M. Sun, S. Kobayashi, J. Am. Chem. Soc. 2002, 124, 11971.
| Crossref | GoogleScholarGoogle Scholar |
(l) S. Shirakawa, S. Kobayashi, Org. Lett. 2007, 9, 311.
| Crossref | GoogleScholarGoogle Scholar |
(m) R. Sanz, A. Martínez, D. Miguel, J. M. Álvarez-Gutiérrez, F. Rodríguez, Adv. Synth. Catal. 2006, 348, 1841.
| Crossref | GoogleScholarGoogle Scholar |
(n) H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. Int. Ed. 2007, 46, 409.
| Crossref | GoogleScholarGoogle Scholar |
(o) V. Terrasson, S. Marque, M. Georgy, J. M. Campagne, D. Prim, Adv. Synth. Catal. 2006, 348, 2063.
| Crossref | GoogleScholarGoogle Scholar |
(p) Y. Lu, X. Fu, H. Chen, X. Du, X. Jia, Y. Liu, Adv. Synth. Catal. 2009, 351, 129.
| Crossref | GoogleScholarGoogle Scholar |
(q) M. H. S. A. Hamid, P. A. Slatford, J. M. J. Williams, Adv. Synth. Catal. 2007, 349, 1555.
| Crossref | GoogleScholarGoogle Scholar |
(r) K. Motokura, N. Nakagiri, T. Mizugaki, K. Ebitani, K. Kaneda, J. Org. Chem. 2007, 72, 6006.
| Crossref | GoogleScholarGoogle Scholar |
(s) K. Motokura, N. Nakagiri, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, K. Kaneda, Org. Lett. 2006, 8, 4617.
| Crossref | GoogleScholarGoogle Scholar |
(t) Y.-M. Pan, F.-J. Zheng, H.-X. Lin, Z.-P. Zhan, J. Org. Chem. 2009, 74, 3148.
| Crossref | GoogleScholarGoogle Scholar |
(u) M. P. Kumar, R.-S. Liu, J. Org. Chem. 2006, 71, 4951.
| Crossref | GoogleScholarGoogle Scholar |
(v) G. W. Wang, Y. B. Shen, X. L. Wu, Eur. J. Org. Chem. 2008, 4367,
| Crossref | GoogleScholarGoogle Scholar |
(w) G. W. Wang, Y. B. Shen, X. L. Wu, Eur. J. Org. Chem. 2008, 4999,
| Crossref | GoogleScholarGoogle Scholar |
[2] (a) P. G. Cozzi, L. Zoli, Angew. Chem. Int. Ed. 2008, 47, 4162.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmslyksL4%3D&md5=94dfee20cfe6666823ef5b077c3b7b86CAS |
(b) P. G. Cozzi, L. Zoli, Green Chem. 2007, 9, 1292.
| Crossref | GoogleScholarGoogle Scholar |
[3] (a) D. R. van Staveren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVGhs7%2FJ&md5=17d41d6e9bb458d2308fafe78722de37CAS |
(b) (b) P. Stepnicka, Ferrocenes: Ligands, Materials and Biomolecules 2008 (John Wiley & Sons: Chichester).
(c) (c) A. Togni, T. Hayashi, Ferrocenes: Homogeneous Catalysis, Organic Synthesis Material Science 1995 (VCH: Weinheim).
(d) J. Brettar, T. Burgi, B. Donnio, D. Guillon, R. Klappert, T. Scharf, R. Deschenaux, Adv. Funct. Mater. 2006, 16, 260.
| Crossref | GoogleScholarGoogle Scholar |
[4] (a) S. I. Klink, H. Keizer, V. Van, J. M. Frank, Angew. Chem. Int. Ed. 2000, 39, 4319.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXovFCgtrk%3D&md5=41c329f7c6923658dc3862db54a3614bCAS |
(b) S. Wu, Y. Chen, F. Zeng, S. Gong, Z. Tong, Macromolecules 2006, 39, 6796.
| Crossref | GoogleScholarGoogle Scholar |
(c) E. Hillard, A. Vessieres, L. Thouin, G. Jaouen, C. Amatore, Angew. Chem. Int. Ed. 2006, 45, 285.
| Crossref | GoogleScholarGoogle Scholar |
(d) G. Tabbì, C. Cassino, G. Cavigiolio, D. Colangelo, A. Ghiglia, I. Viano, D. Osella, J. Med. Chem. 2002, 45, 5786.
| Crossref | GoogleScholarGoogle Scholar |
(e) C. Biot, G. Glorian, L. A. Maciejewski, J. S. Brocard, O. Domarie, G. Blampain, P. Millet, A. J. Georgis, H. Abessolo, D. Dive, J. Lebibi, J. Med. Chem. 1997, 40, 3715.
| Crossref | GoogleScholarGoogle Scholar |
(f) (f) G. Jaouen, N. Metzler-Nolte, Medicinal Organometallic Chemistry 2010 (Springer: Berlin).
[5] (a) F. Fache, E. Schulz, M. L. Tommasino, M. Lemaire, Chem. Rev. 2000, 100, 2159.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3cXjtFKhtr4%3D&md5=bb6ef083f4dd0092530039168497362fCAS |
(b) P. J. Guiry, C. P. Saunders, Adv. Synth. Catal. 2004, 346, 497.
| Crossref | GoogleScholarGoogle Scholar |
(c) O. B. Sutcliffe, M. R. Bryce, Tetrahedron Asymmetry 2003, 14, 2297.
| Crossref | GoogleScholarGoogle Scholar |
(d) (d) M. Perseghini, A. Togni, Science of Synthesis: Houben-Weyl Methods of Molecular Transformation, 2001 (Georg Thieme: Stuttgart).
[6] (a) P. Barbaro, C. Bianchini, G. Giambastiani, S. L. Parisel, Coord. Chem. Rev. 2004, 248, 2131.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVagsL%2FJ&md5=9ed2d3ba48dd31557c9b4cb212411cd6CAS |
(b) P. Debroy, S. Roy, Coord. Chem. Rev. 2007, 251, 203.
| Crossref | GoogleScholarGoogle Scholar |
(c) T. J. Colacot, Chem. Rev. 2003, 103, 3101.
| Crossref | GoogleScholarGoogle Scholar |
(d) R. C. J. Atkinson, V. C. Gibson, N. J. Long, Chem. Soc. Rev. 2004, 33, 313.
| Crossref | GoogleScholarGoogle Scholar |
[7] (a) X. P. Xu, R. Jiang, X. G. Zhou, Y. Liu, S. J. Ji, Y. Zhang, Tetrahedron 2009, 65, 877.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhsFajtLzF&md5=9a961a6e7cd66783fae05262ff958b4dCAS |
(b) R. Jiang, Y. Zhang, Y. C. Shen, X. Zhu, X. P. Xu, S. J. Ji, Tetrahedron 2010, 66, 4073.
| Crossref | GoogleScholarGoogle Scholar |
(c) R. Jiang, X. P. Xu, T. Chen, H. Y. Li, G. Chen, S. J. Ji, Synlett 2009, 2815,
| Crossref | GoogleScholarGoogle Scholar |
[8] (a) T. Chen, X. P. Xu, S. J. Ji, J. Comb. Chem. 2010, 12, 659.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXot1Wntb0%3D&md5=eb5e10f11fefdb20cf989acb80b74a56CAS |
(b) X.-J. Wu, R. Jiang, X. P. Xu, X. M. Su, W. H. Lu, S. J. Ji, J. Comb. Chem. 2010, 12, 829.
| Crossref | GoogleScholarGoogle Scholar |
[9] (a) M. J. Nugent, R. Kummer, J. H. Richards, J. Am. Chem. Soc. 1969, 91, 6141.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1MXlt1eisbs%3D&md5=61a39c0c0cf5f590031dd47e0c9d6615CAS |
(b) M. J. Nugent, R. E. Carter, J. H. Richards, J. Am. Chem. Soc. 1969, 91, 6145.
| Crossref | GoogleScholarGoogle Scholar |
(c) D. Marquarding, H. Klusacek, G. Gokel, P. Hoffman, I. Ugi, J. Am. Chem. Soc. 1970, 92, 5389.
| Crossref | GoogleScholarGoogle Scholar |
(d) G. Gokel, D. Marquarding, I. Ugi, J. Org. Chem. 1972, 37, 3052.
| Crossref | GoogleScholarGoogle Scholar |
(e) R. Gleiter, C. Bleiholder, F. Rominger, Organometallics 2007, 26, 4850.
| Crossref | GoogleScholarGoogle Scholar |
(f) P. Vicennati, P. G. Cozzi, Eur. J. Org. Chem. 2007, 2248,
| Crossref | GoogleScholarGoogle Scholar |
[10] M. Rausch, M. Vogel, H. Rosenberg, J. Org. Chem. 1957, 22, 903.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1cXitFSruw%3D%3D&md5=2a8201e97394289230b236901781b6dfCAS |
[11] M. Cais, A. Eisenstadt, J. Org. Chem. 1965, 30, 1148.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF2MXot1Ojsg%3D%3D&md5=304cce2272809fa6a5366e7fd98c7f87CAS |