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 2013; 45(24): 3387-3391
DOI: 10.1055/s-0033-1339929
DOI: 10.1055/s-0033-1339929
paper
Copper/Imidazolium/TEMPO-Catalyzed Aerobic Oxidation of Benzylic Alcohols in Water
Further Information
Publication History
Received: 30 July 2013
Accepted after revision: 21 September 2013
Publication Date:
09 October 2013 (online)
Abstract
Various imidazolium salts bearing hydrophilic groups were prepared that reacted with copper powder to afford water-soluble copper complexes of N-heterocyclic carbenes. These copper complexes can catalyze the selective oxidation of benzyl alcohols to the corresponding aldehydes in water at room temperature without the need for a base.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Aqueous-Phase Organometallic Catalysis: Concepts and Applications. Cornils B, Herrmann WA. Wiley-VCH; Weinheim: 2004
- 2 Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
- 3 ten Brink G.-J, Arends IW. C. E, Sheldon RA. Science (Washington, D.C.) 2000; 287: 1636
- 4 Punniyamurthy T, Laxmidhar R. Coord. Chem. Rev. 2008; 252: 134
- 5 Maclennan A, Banerjee A, Scott RW. J. Catal. Today 2013; 207: 170
- 6 Komiya N, Nakae T, Sato H, Naota T. Chem. Commun. 2006; 46: 4829
- 7 Verho O, Dilenstam MD. V, Kärkäs MD, Johnston EV, Åkermark T, Bäckvall JE, Åkermark B. Chem. Eur. J. 2012; 18: 16947
- 8 Herrmann WA. Angew. Chem. Int. Ed. 2002; 41: 1290
- 9 de Fremont P, Marion N, Nolan SP. Coord. Chem. Rev. 2009; 253: 862
- 10a Velazquez HD, Verpoort F. Chem. Soc. Rev. 2012; 41: 7032
- 10b Schaper LA, Hock SJ, Herrmann WA, Kuhn FE. Angew. Chem. Int. Ed. 2013; 52: 270
- 11 Allen SE, Walvoord RR, Salinas RP, Kozlowski MC. Chem. Rev. 2013; 113: 6234
- 12a Liu B, Xia QQ, Chen W. Angew. Chem. Int. Ed. 2009; 48: 5513
- 12b Liu B, Liu B, Zhou YB, Chen W. Organometallics 2010; 29: 1457
- 12c Liu B, Xu DC, Chen WZ. Chem. Commun. 2011; 47: 2883
- 12d Liu X, Xia Q, Zhang Y, Chen C, Chen W. J. Org. Chem. 2013; 78: 8531
- 13a Liu A, Zhang X, Chen W. Organometallics 2009; 28: 4868
- 13b Zhang X, Xia Q, Chen W. Dalton Trans. 2009; 7045
- 13c Xi Z, Liu B, Lu C, Chen W. Dalton Trans. 2009; 7008
- 13d Zhang X, Gu S, Xia Q, Chen W. J. Organomet. Chem. 2009; 694: 2359
- 14a Papini G, Pellei M, Lobbia GG, Burini A, Santini C. Dalton Trans. 2009; 6985
- 14b Godoy F, Segarra C, Peris E. Organometallics 2011; 30: 684
- 15a Gamez P, Arends IW. C. E, Reedijk J, Sheldon RA. Chem. Commun. 2003; 2414
- 15b Gamez P, Arends IW. C. E, Sheldon RA, Reedijk J. Adv. Synth. Catal. 2004; 346: 805
- 16 Zhu Y, Zhao B, Shi Y. Org. Lett. 2013; 15: 992
- 17 Ragagnin G, Betzemeier B, Quici S, Knochel P. Tetrahedron 2002; 58: 3985
- 18 Jiang N, Ragauskas AJ. Org. Lett. 2005; 7: 3689
- 19 Hoover JM, Stahl SS. J. Am. Chem. Soc. 2011; 133: 16901
- 20 Miao CX, Wang JQ, He LN, Zhang SJ. Chem. Commun. 2011; 47: 2697
- 21 Nath P, Punniyamurthy T. Adv. Synth. Catal. 2007; 349: 846
- 22 Pérez LJ. M, Cano R, Yus M, Ramón DJ. Eur. J. Org. Chem. 2012; 4548
- 23 Rauniyar V, Hall DG. J. Org. Chem. 2009; 74: 4236
- 24 Sun H.-y, Huang W.-x. Adv. Synth. Catal. 2012; 354: 569
- 25 Gregg BT, Quinn JF. J. Org. Chem. 2007; 72: 5890