RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2015; 47(12): 1749-1760
DOI: 10.1055/s-0034-1380155
DOI: 10.1055/s-0034-1380155
paper
Synthesis of Ethers from Carbonyl Compounds by Reductive Etherification Catalyzed by Iron(III) and Silyl Chloride
Authors
Weitere Informationen
Publikationsverlauf
Received: 07. November 2014
Accepted after revision: 15. Januar 2015
Publikationsdatum:
18. Februar 2015 (online)
Abstract
A simple iron- and silyl chloride catalyzed method for the preparation of symmetrical and nonsymmetrical ethers is presented. Various aldehydes and ketones were reductively etherified by using triethylsilane as a reducing agent in the presence of 2 mol% of iron(III) oxo acetate and 8 mol% of chloro(trimethyl)silane. The reactions can be carried out at ambient temperatures and pressures with ethyl acetate as the solvent.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380155.
Included are details on catalyst preparation and characterization and copies of NMR
and GC chromatograms of the isolated products.
- Supporting Information (PDF)
-
References
- 2 Wurtz A. Ann. Chim. Phys. 1856; 46 [3]: 222
- 3a Doyle MP, DeBruyn DJ, Kooistra DA. J. Am. Chem. Soc. 1972; 94: 3659
- 3b West CT, Donnely SJ, Kooistra DA, Doyle MP. J. Org. Chem. 1973; 38: 2675
- 3c Doyle MP, DeBruyn DJ, Donnely SJ, Kooistra DA, Odubela AO, West CT, Zonnebelt SM. J. Org. Chem. 1974; 39: 2740
- 3d Doyle MP, West CT. J. Org. Chem. 1975; 40: 3821
- 3e Doyle MP, West CT. J. Org. Chem. 1975; 40: 3829
- 3f Doyle MP, West CT. J. Org. Chem. 1975; 40: 3835
- 4 Tsunoda T, Suzuki M, Noyori R. Tetrahedron Lett. 1979; 20: 4679
- 5 Kato J, Iwasawa N, Mukaiyama T. Chem. Lett. 1985; 743
- 6 Sassaman MB, Kotian KD, Surya Prakash GK, Olah GA. J. Org. Chem. 1987; 52: 4314
- 7 Doyle MP, West CT, Donnely SJ, McOsker CC. J. Organomet. Chem. 1976; 117: 129
- 8 Aizpurua JM, Lecea B, Palomo C. Can. J. Chem. 1986; 64: 2342
- 9a Wada M, Nagayama S, Mizutani K, Hiroi R, Miyoshi N. Chem. Lett. 2002; 31: 248
- 9b Komatsu N, Ishida J.-y, Suzuki H. Tetrahedron Lett. 1997; 38: 7219
- 10 Sakai N, Nagasawa K, Ikeda R, Nakaike Y, Konakahara T. Tetrahedron Lett. 2011; 52: 3133
- 11a Olah GA, Arvanaghi M, Ohannesian L. Synthesis 1986; 770
- 11b Nishiyama T, Kameyama H, Maekawa H, Watanuki K. Can. J. Chem. 1999; 77: 258
- 11c Gellert BA, Kahlcke N, Feurer M, Roth S. Chem. Eur. J. 2011; 17: 12203
- 12a Olah GA, Yamato T, Iyer PS, Surya Prakash GK. J. Org. Chem. 1986; 51: 2826
- 12b Onaka M, Higuchi K, Nanami H, Izumi Y. Bull. Chem. Soc. Jpn. 1993; 66: 2638
- 13 Yadav JS, Subba Reddy BV, Shiva Shankar K, Swamy T. Tetrahedron Lett. 2010; 51: 46
- 14 Zhang Y.-J, Dayoub W, Chen G.-R, Lemaire M. Tetrahedron 2012; 68: 7400
- 15 Baek JY, Lee SJ, Han BH. J. Korean Chem. Soc. 2004; 48: 220
- 16 Sakai N, Nomomura Y, Ikeda R, Konakahara T. Chem. Lett. 2013; 42: 489
- 17a Bolm C, Legros J, Le Paith J, Zani L. Chem. Rev. 2004; 104: 6217
- 17b Correa A, Mancheño OG, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
- 17c Bauer EB. Curr. Org. Chem. 2008; 12: 1341
- 17d Sun X, Li J, Huang X, Sun C. Curr. Inorg. Chem. 2012; 2: 64
- 17e Sun C.-L, Li B.-J, Sun Z.-J. Chem. Rev. 2011; 111: 1293
- 18a Gaillard S, Renaud J.-L. ChemSusChem 2008; 1: 505
- 18b Morris RH. Chem. Soc. Rev. 2009; 38: 2282
- 18c Zhang M, Zhang A. Appl. Organomet. Chem. 2010; 24: 751
- 18d Junge K, Schröder K, Beller M. Chem. Commun. 2011; 47: 4849
- 18e Le Bailly BA. F, Thomas SP. RSC Adv. 2011; 1: 1435
- 19a Tondreau AM, Darmon JM, Wile BM, Floyd SK, Lobkovsky E, Chirik PJ. Organometallics 2009; 28: 3928
- 19b Inagaki T, Thanh Phong L, Furuta A, Ito J.-i, Nishiyama H. Chem. Eur. J. 2010; 16: 3090
- 19c Inagaki T, Ito A, Ito J.-i, Nishiyama H. Angew. Chem. Int. Ed. 2010; 49: 9384
- 19d Addis D, Shaikh N, Zhou S, Das S, Junge K, Beller M. Chem. Asian J. 2010; 5: 1687
- 19e Kandepi VV. K. M, Cardoso JM. S, Peris E, Royo B. Organometallics 2010; 29: 2777
Reference Ris Wihthout Link
- 19f Yang J, Tilley TD. Angew. Chem. Int. Ed. 2010; 49: 10186
- 19g Buitrago E, Zani L, Adolfsson H. Appl. Organomet. Chem. 2011; 25: 748
- 19h Jiang F, Bézier D, Sortais J.-B, Darcel C. Adv. Synth. Catal. 2011; 353: 239
- 19i Misal Castro LC, Bézier D, Sortais J.-B, Darcel C. Adv. Synth. Catal. 2011; 353: 1279
- 19j Buitrago E, Tinnis F, Adolfsson H. Adv. Synth. Catal. 2012; 354: 217
- 19k Hashimoto T, Urban S, Hoshino R, Ohki Y, Tatsumi K, Glorius F. Organometallics 2012; 31: 4474
Reference Ris Wihthout Link
- 19l Grohmann C, Hashimoto T, Fröhlich R, Ohki Y, Tatsumi K, Glorius F. Organometallics 2012; 31: 8047
- 19m Misal Castro LC, Li H, Sortais J.-B, Darcel C. Chem. Commun. 2012; 48: 10514
- 19n Ruddy AJ, Kelly CM, Crawford SM, Wheaton CA, Sydora OL, Small BL, Stradiotto M, Turculet L. Organometallics 2013; 32: 5581
- 19o Lopes R, Cardoso JM. S, Postigo L, Royo B. Catal. Lett. 2013; 143: 1061
- 19p Wu S, Li X, Xiong Z, Xu W, Lu Y, Sun H. Organometallics 2013; 32: 3227
- 19q Junge K, Wendt B, Zhou S, Beller M. Eur. J. Org. Chem. 2013; 2061
- 20a Zhou S, Junge K, Addis D, Das S, Beller M. Angew. Chem. Int. Ed. 2009; 48: 9507
- 20b Sunada Y, Kawakami H, Imaoka T, Motoyama Y, Nagashima H. Angew. Chem. Int. Ed. 2009; 48: 9511
- 20c Das S, Zhou S, Addis D, Enthaler S, Junge K, Beller M. Top. Catal. 2010; 53: 979
- 20d Tsutsumi H, Sunada Y, Nagashima H. Chem. Commun. 2011; 47: 6581
- 20e Bézier D, Venkanna GT, Sortais J.-B, Darcel C. ChemCatChem 2011; 3: 1747
- 20f Misal Castro LC, Sortais J.-B, Darcel C. Chem. Commun. 2012; 48: 151
- 20g Das S, Wendt B, Möller K, Junge K, Beller M. Angew. Chem. Int. Ed. 2012; 51: 1662
- 20h Volkov A, Buitrago E, Adolfsson H. Eur. J. Org. Chem. 2013; 2066
- 21 Guo X.-K, Zhao D.-Y, Li J.-H, Zhang X.-G, Deng C.-L, Tang R.-Y. Synlett 2012; 627
- 22a Iovel I, Mertins K, Kischel K, Zapf A, Beller M. Angew. Chem. Int. Ed. 2005; 44: 3913
- 22b Kischel J, Jovel I, Mertins K, Zapf A, Beller M. Org. Lett. 2006; 8: 19
- 22c Gao J, Wang J.-Q, Song Q.-W, He L.-N. Green Chem. 2011; 13: 1182
- 22d Sawama Y, Shishido Y, Kawajiri T, Goto R, Monguchi Y, Sajiki H. Chem. Eur. J. 2014; 20: 510
- 22e Pan X, Li M, Gu Y. Chem. Asian J. 2014; 9: 268
- 23a Chunqi S, Zhifang L, Guoqiao L, Jianxiong J, Wendong X, Xiaojun C. CN 1880289, 2006
- 23b Chun-Qi S, Zhi-Fang L, Cheng-Jun Y, Guo-Qiao L, Huan-Yu Q. Youji Huaxue 2008; 28: 515
- 23c Li Z, Sheng C, Qiu H, Zhang Y. Org. Prep. Proced. Int. 2007; 39: 412
- 24 Sawama Y, Nagata S, Yabe Y, Morita K, Monguchi Y, Sajiki H. Chem. Eur. J. 2012; 18: 16608
- 25a Iwanami K, Seo H, Tobita Y, Oriyama T. Synthesis 2005; 183
- 25b Iwanami K, Yano K, Oriyama T. Chem. Lett. 2007; 36: 38
- 26a Das S, Li Y, Junge K, Beller M. Chem. Commun. 2012; 48: 10742
- 26b Bézier D, Venkana GT, Misal Castro LC, Zheng J, Roisnel T, Sortais J.-B, Darcel C. Adv. Synth. Catal. 2012; 354: 1879
- 27 Savela R, Majewski M, Leino R. Eur. J. Org. Chem. 2014; 4137
- 28 Savela, R.; Wärnå, J.; Murzin, D. Yu.; Leino, R. Catal. Sci. Technol. 2015, in press; DOI: 10.1039/C5CY00067J.
- 29a Orgel LE. Nature 1960; 187: 504
- 29b Figgis BN, Robertson GB. Nature 1965; 205: 694
- 29c Ciavatta L, Nunziata G, Sillén LG. Acta Chem. Scand. 1969; 23: 1637
- 29d Paul RC, Narula RC, Vasisht SK. Transition Met. Chem. 1978; 3: 35
- 29e Oh SM, Hendrickson DN, Hassett KL, Davis RE. J. Am. Chem. Soc. 1984; 106: 7984
- 29f Blake AB, Yavari A, Hatfield WE, Sethulekshmi CN. J. Chem. Soc., Dalton Trans. 1985; 2509
- 29g Sorai M, Shiomi Y, Hendrickson DN, Oh SM, Kambara T. Inorg. Chem. 1987; 26: 223
- 29h Arora K, Bhatnagar P, Bhargava AP, Gupta YK. J. Chem. Soc., Dalton Trans. 1991; 1081
- 29i Sato T, Ambe F, Endo K, Katada M, Maeda H, Nakamoto T, Sano H. J. Am. Chem. Soc. 1996; 118: 3450
- 30 Molander GA, Canturk B. Org. Lett. 2008; 10: 2135
- 31 Yamato T, Hu J.-Y, Shinoda N. J. Chem. Res. 2007; 641
- 32 Kalviri HA, Kerton FM. Adv. Synth. Catal. 2011; 353: 3178
- 33 Felstead R, Gibson SE, Rooney A, Tse ES. Y. Eur. J. Org. Chem. 2008; 4963
- 34 Funke U, Jia H, Fischer S, Scheunemann M. J. Labelled Compd. Radiopharm. 2006; 49: 745
- 35 Riad Y, Gundermann KD, El Bardan AA. Egypt. J. Chem. 1994; 37: 123
- 36 Waddell DC, Thiel I, Clark TD, Marcum ST, Mack J. Green Chem. 2010; 12: 209
- 37 Tuchinda P, Undchachon J, Khumtaveeporn K, Taylor WC. Phytochemistry 1989; 28: 2463
- 38 Smith MA, Weinstein B, Greene FD. J. Org. Chem. 1980; 45: 4597
- 39 Belema M, Hewawasam P. US 20110237636, 2011
- 40 Takasaki M, Motoyama Y, Higashi K, Yoon S.-H, Mochida I, Nagashima H. Chem. Asian J. 2007; 2: 1524
- 41 Molander GA, Beaumard F. Org. Lett. 2011; 13: 3948
- 42 Madhavan N, Gin MS. Chem. Commun. 2004; 2728
- 43 Alonso F, Barba I, Yus M. Tetrahedron 1990; 46: 2069
- 44 Yoshida K, Toyoshima T, Imamoto T. Chem. Commun. 2007; 3774
- 45 Vo C.-VT, Mitchell TA, Bode JW. J. Am. Chem. Soc. 2011; 133: 14082
- 46 Lipshutz BH, Parker D, Kozlowski JA, Miller RD. J. Org. Chem. 1983; 48: 3334
- 47 Shen Z, Sheng L, Zhang X, Mo W, Hu B, Sun N, Hu X. Tetrahedron Lett. 2013; 54: 1579
- 48 Fujii Y, Furugaki H, Tamura E, Yano S, Kita K. Bull. Chem. Soc. Jpn. 2005; 78: 456
- 49 Pollex A, Hiersemann M. Org. Lett. 2005; 7: 5705
- 50 van Rijn JA, Guijt MC, de Vries D, Bouwman E, Drent E. Appl. Organomet. Chem. 2011; 25: 212
- 51 Onishi Y, Ogawa D, Yasuda M, Baba A. J. Am. Chem. Soc. 2002; 124: 13690
- 52a Miyai T, Onishi Y, Baba A. Tetrahedron Lett. 1998; 39: 6291
- 52b Miyai T, Onishi Y, Baba A. Tetrahedron 1999; 55: 1017
- 53a Mukaiyama T, Ohno T, Nishimura T, Han JS, Kobayashi S. Chem. Lett. 1990; 2239
- 53b Saito T, Nishimoto Y, Yasuda M, Baba A. J. Org. Chem. 2006; 71: 8516
- 54a Larson GL, Fry JL. Org. React. (N. Y.) 2008; 71: 1
- 54b Klare HF. T, Oestreich M. Dalton Trans. 2010; 39: 9176
- 55 Shaterian HR, Ghashang M, Hosseinian A. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 171
- 56 Errede LA. J. Am. Chem. Soc. 1961; 83: 949
- 57 Leonard AG. G. J. Chem. Soc., Trans. 1916; 109: 570
- 58 Kikugawa Y, Ogawa Y. Chem. Pharm. Bull. 1979; 27: 2405
- 59 The NMR spectra reported for this compound here is not fully consistent with the incomplete analysis reported (see ref. 8). Because of the presence of persistent traces of ethyl acetate in the isolated sample, elemental analysis was not suitable for verification of the identity of the product or its elemental composition. In ESI-HRMS, strong chelation effects were observed, further hampering analysis of the product by an independent method. The identity of the free phenolic product was eventually verified by trimethylsilyl derivatization for GC analysis.
- 60 Goldenberg M, Emert J, Morawetz H. J. Am. Chem. Soc. 1978; 100: 7171
- 61 Tsai SC, Klinman JP. Bioorg. Chem. 2003; 31: 172
For reviews, see:
For reviews, see: