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 2016; 48(23): 4143-4148
DOI: 10.1055/s-0035-1562542
DOI: 10.1055/s-0035-1562542
paper
Indium(III) Isopropoxide as a Hydrogen Transfer Catalyst for Conversion of Benzylic Alcohols into Aldehydes or Ketones via Oppenauer Oxidation
Further Information
Publication History
Received: 28 June 2016
Accepted after revision: 22 July 2016
Publication Date:
01 September 2016 (online)
Abstract
Indium(III) isopropoxide [In(Oi-Pr)3] was applicable as an Oppenauer oxidation catalyst, and the conversion of primary or secondary alcohols into the corresponding aldehydes or ketones was promoted at room temperature using pivalaldehyde as an oxidant.
Key words
indium catalyst - Oppenauer oxidation - primary alcohol - secondary alcohol - aldehyde - ketone - room temperatureSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562542.
- Supporting Information
-
References
- 1a Graves CR, Campbell EJ, Nguyen ST. Tetrahedron: Asymmetry 2005; 16: 3460
- 1b Ooi T, Miura T, Itagaki Y, Ichikawa H, Maruoka K. Synthesis 2002; 279
- 1c de Graauw CF, Peters JA, van Bekkum H, Huskens J. Synthesis 1994; 1007
- 2a Namy JL, Souppe J, Collin J, Kagan HB. J. Org. Chem. 1984; 49: 2045
- 2b Ishii Y, Nakano T, Inada A, Kishigami Y, Sakurai K, Ogawa M. J. Org. Chem. 1986; 51: 240
- 2c Krohn K, Knauer B, Küpke J, Seebach D, Beck AK, Hayakawa M. Synthesis 1996; 1341
- 2d Ishihara K, Kurihara H, Yamamoto H. J. Org. Chem. 1997; 62: 5664
- 2e Ooi T, Otsuka H, Miura T, Ichikawa H, Maruoka K. Org. Lett. 2002; 4: 2669
- 2f Graves CR, Zeng B.-S, Nguyen ST. J. Am. Chem. Soc. 2006; 128: 12596
- 3a Suzuki T, Morita K, Tsuchida M, Hiroi K. J. Org. Chem. 2003; 68: 1601
- 3b Gauthier S, Scopelliti R, Severin K. Organometallics 2004; 23: 3769
- 3c Moyer SA, Funk TW. Tetrahedron Lett. 2010; 51: 5430
- 3d Johnson TC, Clarkson GJ, Wills M. Organometallics 2011; 30: 1859
- 3e Fujita K.-i, Uejima T, Yamaguchi R. Chem. Lett. 2013; 42: 1496
- 3f Prakash O, Sharma KN, Joshi H, Gupta PL, Singh AK. Organometallics 2014; 33: 983
- 4 Lee J, Ryu T, Park S, Lee PH. J. Org. Chem. 2012; 77: 4821
- 5 Normand M, Kirillov E, Roisnel T, Carpentier J.-F. Organometallics 2012; 31: 5511
- 6 Ogiwara Y, Kubota M, Kurogi K, Konakahara T, Sakai N. Chem. Eur. J. 2015; 21: 18598
- 7a Augé J, Lubin-Germain N, Seghrouchni L. Tetrahedron Lett. 2002; 43: 5255
- 7b Augé J, Lubin-Germain N, Seghrouchni L. Tetrahedron Lett. 2003; 44: 819
- 8 Jung HM, Choi JH, Lee SO, Kim YH, Park JH, Park J. Organometallics 2002; 21: 5674
- 9 Hong B.-C, Tseng H.-C, Chen S.-H. Tetrahedron 2007; 63: 2840
- 10 Lee K, Maleczka RE. Jr. Org. Lett. 2006; 8: 1887
- 11 Zhu C, Yukimura N, Yamane M. Organometallics 2010; 29: 2098
- 12 Inokuchi T, Matsumoto S, Fukushima M, Torii S. Bull. Chem. Soc. Jpn. 1991; 64: 796
- 13 Magano J, Chen MH, Clark JD, Nussbaumer T. J. Org. Chem. 2006; 71: 7103
- 14 Koren-Selfridge L, Londino HN, Vellucci JK, Simmons BJ, Casey CP, Clark TB. Organometallics 2009; 28: 2085
- 15 Lin C.-K, Lu T.-J. Tetrahedron 2010; 66: 9688
- 16 Kim BR, Lee H.-G, Kim EJ, Lee S.-G, Yoon Y.-J. J. Org. Chem. 2010; 75: 484
- 17 Pelletier G, Bechara WS, Charette AB. J. Am. Chem. Soc. 2010; 132: 12817
- 18 Velusamy S, Ahamed M, Punniyamurthy T. Org. Lett. 2004; 6: 4821
Selected reviews of Oppenauer oxidation: