Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2014; 46(05): 629-634
DOI: 10.1055/s-0033-1340498
DOI: 10.1055/s-0033-1340498
paper
Fe(Cp)2BF4: An Efficient Lewis Acid Catalyst for the Aminolysis of Epoxides
Further Information
Publication History
Received: 18 September 2013
Accepted after revision: 09 December 2013
Publication Date:
08 January 2014 (online)
![](https://www.thieme-connect.de/media/synthesis/201405/lookinside/thumbnails/10.1055-s-0033-1340498-1.jpg)
Abstract
Ferrocenium tetrafluoroborate [Fe(Cp)2BF4] is an efficient Lewis acid catalyst for the aminolysis of aromatic, aliphatic, and cyclic epoxides using aniline and substituted anilines as the nucleophile to provide regioselective β-amino alcohols in 61–97% yields under solvent-free conditions at room temperature. The ring opening of cyclohexene oxide with aliphatic amines gave 2-aminocyclohexanols in 33–98% yields at 60 °C under solvent-free conditions.
-
References
- 1a Ager DJ, Prakash I, Schaad DR. Chem. Rev. 1996; 96: 835
- 1b Corey EJ, Zhang F.-Y. Angew. Chem. Int. Ed. 1999; 38: 1931
- 1c Johannes CW, Visser MS, Weatherhead GS, Hoveyda AH. J. Am. Chem. Soc. 1998; 120: 8340
- 1d Chng BL, Ganesan A. Bioorg. Med. Chem. Lett. 1997; 7: 1511
- 1e Alonso DA, Guijarro D, Pinho P, Temme O, Andersson PG. J. Org. Chem. 1998; 63: 2749
- 1f Castejon P, Moyano A, Pericas MA, Riera A. Tetrahedron 1996; 52: 7063
- 1g Li G, Chang H.-T, Sharpless KB. Angew. Chem. Int. Ed. 1996; 35: 451
- 2a Hodgson DM, Gibbs AR, Lee GP. Tetrahedron 1996; 52: 14361
- 2b Bergmeier SC. Tetrahedron 2000; 56: 2561
- 3a Deyrup JA, Moyer CL. J. Org. Chem. 1969; 34: 175
- 3b Freifelder M, Stone GR. J. Org. Chem. 1961; 26: 1477
- 3c Lutz RE, Freekand JA, Murphy RS. J. Am. Chem. Soc. 1948; 70: 2015
- 3d Rao AS, Paknikar SK, Kirtane JG. Tetrahedron 1983; 39: 2323
- 3e Hanson RM. Chem. Rev. 1991; 91: 437
- 4a CoCl2: Iqbal J, Pandey A. Tetrahedron Lett. 1990; 31: 575
- 4b SmI2: Van de Weghe P, Collin J. Tetrahedron Lett. 1995; 36: 1649
- 4c SmCl3: Fu X.-L, Wu S.-H. Synth. Commun. 1997; 27: 1677
- 4d TaCl5: Chandrasekhar S, Ramchander T, Prakash SJ. Synthesis 2000; 1817
- 4e CeCl3: Reddy LR, Reddy MA, Bhanumathi N, Rao KR. Synthesis 2000; 831
- 4f BiCl3: Ollevier T, Lavie-Compin G. Tetrahedron Lett. 2002; 43: 7891
- 4g BiCl3: Swamy NR, Kandaji G, Nagaiah G. Synth. Commun. 2002; 32: 2307
- 4h (C4H12N2)2[BiCl6]Cl·H2O: Lu H.-F, Sun L.-L, Le W.-J, Yang F.-F, Zhou J.-T, Gao Y.-H. Tetrahedron Lett. 2012; 53: 4267
- 4i ZnCl2: Pachón LD, Gamez P, Van Brussel JJ. M, Reedijk J. Tetrahedron Lett. 2003; 44: 6025
- 4j VCl3: Sabitha G, Reddy GS. K. K, Reddy KB, Yadav JS. Synthesis 2003; 2298
- 4k ZrCl4: Chakraborti AK, Kondaskar A. Tetrahedron Lett. 2003; 44: 8315
- 4l InBr3: Rodríguez JR, Navarro A. Tetrahedron Lett. 2004; 45: 7495
- 4m IrCl3: Agarwal J, Duley A, Rani R, Peddinti RK. Synlett 2009; 2790
- 5a Ph4SbOTf: Fujiwara M, Imada M, Baba A, Matsuda H. Tetrahedron Lett. 1989; 30: 739
- 5b Ln(OTf)3: Chini M, Crotti P, Favero L, Macchia F, Pineschi M. Tetrahedron Lett. 1994; 35: 433
- 5c Yb(OTf)3: Meguro M, Asao N, Yamamoto Y. J. Chem. Soc., Perkin Trans. 1 1994; 2597
- 5d LiOTf: Augé J, Leroy F. Tetrahedron Lett. 1996; 37: 7715
- 5e Cu(OTf)2: Sekar G, Singh VK. J. Org. Chem. 1999; 64: 287
- 5f Bi(OTf)3: Ollevier T, Lavie-Compin G. Tetrahedron Lett. 2004; 45: 49
- 5g Sm(OTf)3: Yadav JS, Reddy AR, Narsaiah AV, Reddy BV. S. J. Mol. Catal. A: Chem. 2007; 261: 207
- 6a Ti(Oi-Pr)4: Sagava S, Abe H, Hase Y, Inaba T. J. Org. Chem. 1999; 64: 4962
- 6b Diisopropoxyaluminum trifluoroacetate: Rampalli S, Chaudhari SS, Akamanchi KG. Synthesis 2000; 78
- 6c Al[OC(CF3)2R]3: Li Y, Tan Y, Herdtwick E, Cokoja M, Kühn FE. Appl. Catal., A 2010; 384: 171
- 7a Et2AlNHR: Overman LE, Flippin LA. Tetrahedron Lett. 1981; 22: 196
- 7b Silicon amides: Papini A, Ricci I, Taddei M, Seconi G, Dembach P. J. Chem. Soc., Perkin Trans. 1 1984; 2261
- 7c R2NMgBr: Carre MC, Houmounou JP, Caubere P. Tetrahedron Lett. 1985; 26: 3107
- 7d R1 3PbNR2 2: Yamada J.-I, Yumoto M, Yamamoto Y. Tetrahedron Lett. 1989; 30: 4255
- 7e Cu amide: Yamamoto Y, Asao N, Meguro M, Tsukade N, Nemoto H, Adayari N, Wilson JG, Nakamura H. J. Chem. Soc., Chem. Commun. 1993; 1201
- 7f LiNTf2: Cossy J, Bellosta V, Hamoir C, Desmurs J.-R. Tetrahedron Lett. 2002; 43: 7083
- 8a Chini M, Crotti P, Macchia F. Tetrahedron Lett. 1990; 31: 4661
- 8b Zhao P.-Q, Xu L.-W, Xia C.-G. Synlett 2004; 846
- 8c CuBF4: Kamal A, Ramu R, Azhar MA, Khanna GB. R. Tetrahedron Lett. 2005; 46: 2675
- 8d Y(NO3)3·6H2O: Bhanushali MJ, Nandurkar NS, Bhor MD, Bhanage BM. Tetrahedron Lett. 2008; 49: 3672
- 9 Das U, Crousse B, Kesavan V, Bonnet-Delpon D, Bégué J-P. J. Org. Chem. 2000; 65: 6749
- 10 Yadav JS, Reddy BV. S, Basak AK, Narasaiah AV. Tetrahedron Lett. 2003; 44: 1047
- 11 Curini M, Epifano F, Marcotullio MC, Rosati O. Eur. J. Org. Chem. 2001; 4149
- 12a Mojtahedi MM, Saidi MR, Bolourtchian M. J. Chem. Res., Synop. 1999; 128
- 12b Chakraborti AK, Kondaskar A, Rudrawar S. Tetrahedron 2004; 60: 9085
- 13 Najmodin A, Mohammad RS. Org. Lett. 2005; 17: 3649
- 14a Kotsuki H, Shimanouchi T, Teraguchi M, Kataoka M, Tatsukawa A, Nishizawa H. Chem. Lett. 1994; 2159
- 14b Chakraborti AK, Rudrawar S, Kondaskar A. Org. Biomol. Chem. 2004; 2: 1277
- 15a Posner GH, Roger DZ. J. Am. Chem. Soc. 1977; 99: 8208
- 15b Pujol MD, Harrak Y. Tetrahedron Lett. 2002; 43: 819
- 15c Xue WM, Kung MC, Kozlov AI, Popp KE, Kung HH. Catal. Today 2003; 85: 219
- 16 Kureshy RI, Singh S, Khan NH, Abdi SH. R, Suresh E, Jasra RV. J. Mol. Catal. A: Chem. 2007; 264: 162
- 17 Heravi MM, Baghernejad B, Oskooie HA. Catal. Lett. 2009; 130: 547
- 18 Saikia L, Satyarthi JK, Srinivas D, Ratnasamy P. J. Catal. 2007; 252: 148
- 19 Kumar G, Singh AP, Gupta R. Eur. J. Inorg. Chem. 2010; 5103
- 20 Krishnan GR, Sreekumar K. Polymer 2008; 49: 5233
- 21 Wei S, Stingl KA, Weiß KM, Tsogoeva SB. Synlett 2010; 707
- 22a Khan NH, Agrawal S, Kureshy RI, Abdi SH. R, Singh S, Jasra RV. J. Organomet. Chem. 2007; 692: 4361
- 22b Khan NH, Agrawal S, Kureshy RI, Abdi SH. R, Singh S, Jasra RV. Tetrahedron Lett. 2008; 49: 640
- 23 Plancq B, Ollevier T. Chem. Commun. 2012; 48: 3806
- 24 Nishida A, Shirato F, Nakagawa M. Tetrahedron: Asymmetry 2000; 11: 3789
A variety of metal salts: