Direct C–O Bond Activation Mediated by AcOH: A New Metal-Free Way for α-Functionalization of Ferrocene Alcohols

作者: Ran Jiang , Xue-Qiang Chu , Xiao-Ping Xu , Bin Wu , Shun-Jun Ji

DOI: 10.1071/CH11167

关键词: BiocatalysisAcetic acidCatalysisChemistryOrganic chemistrySupramolecular chemistryReaction mechanismGreen chemistryMethyleneCombinatorial chemistryFerrocene

摘要: α-functionalization of ferrocenyl alcohols by direct C–O bond activation indoles, active methylene compounds, electron-rich arenes, anilines, alcohols, and thiols in acetic acid is described. This protocol provides a relatively green efficient combinatorial access to ferrocene derivatives metal-free manner.

参考文章(51)
Giovanni Tabbì, Claudio Cassino, Giorgio Cavigiolio, Donato Colangelo, Annalisa Ghiglia, Ilario Viano, Domenico Osella, Water stability and cytotoxic activity relationship of a series of ferrocenium derivatives. ESR insights on the radical production during the degradation process. Journal of Medicinal Chemistry. ,vol. 45, pp. 5786- 5796 ,(2002) , 10.1021/JM021003K
Ran Jiang, Ying Zhang, Ye-Chen Shen, Xu Zhu, Xiao-Ping Xu, Shun-Jun Ji, Nucleophilic substitution of ferrocenyl alcohols by cerium ammonium nitrate: C–N, C–S, and C–O bonds formation Tetrahedron. ,vol. 66, pp. 4073- 4078 ,(2010) , 10.1016/J.TET.2010.04.015
J. Brettar, T. Bürgi, B. Donnio, D. Guillon, R. Klappert, T. Scharf, R. Deschenaux, Ferrocene-Containing Optically Active Liquid-Crystalline Side-Chain Polysiloxanes with Planar Chirality Advanced Functional Materials. ,vol. 16, pp. 260- 267 ,(2006) , 10.1002/ADFM.200500223
Christophe Biot, Guillaume Glorian, Lucien A. Maciejewski, Jacques S. Brocard, Olivier Domarle, Georgette Blampain, Pascal Millet, Alain J. Georges, Huguette Abessolo, Daniel Dive, Jacques Lebibi, Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue. Journal of Medicinal Chemistry. ,vol. 40, pp. 3715- 3718 ,(1997) , 10.1021/JM970401Y
Patrick J. Guiry, Cormac P. Saunders, The Development of Bidentate P,N Ligands for Asymmetric Catalysis Advanced Synthesis & Catalysis. ,vol. 346, pp. 497- 537 ,(2004) , 10.1002/ADSC.200303138
Kei Manabe, Shinya Iimura, Xiang-Min Sun, Shū Kobayashi, Dehydration reactions in water. Brønsted Acid-surfactant-combined catalyst for ester, ether, thioether, and dithioacetal formation in water. Journal of the American Chemical Society. ,vol. 124, pp. 11971- 11978 ,(2002) , 10.1021/JA026241J
Pierluigi Barbaro, Claudio Bianchini, Giuliano Giambastiani, Sébastien L. Parisel, Progress in stereoselective catalysis by metal complexes with chiral ferrocenyl phosphines Coordination Chemistry Reviews. ,vol. 248, pp. 2131- 2150 ,(2004) , 10.1016/J.CCR.2004.03.022
Dave R. van Staveren, Nils Metzler-Nolte, Bioorganometallic Chemistry of Ferrocene Chemical Reviews. ,vol. 104, pp. 5931- 5955 ,(2004) , 10.1021/CR0101510