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 2017; 49(13): 2980-2984
DOI: 10.1055/s-0036-1588993
DOI: 10.1055/s-0036-1588993
paper
Synthesis of β-Nitro Ketones by Chemoselective Reduction of β-Nitro Enones under Solid Heterogeneous Catalysis
Further Information
Publication History
Received: 07 February 2017
Accepted after revision: 13 March 2017
Publication Date:
18 April 2017 (online)
![](https://www.thieme-connect.de/media/synthesis/201713/lookinside/thumbnails/ss-2017-z0081-op_10-1055_s-0036-1588993-1.jpg)
Abstract
A new, simple and efficient chemoselective reduction of β-nitro enones to provide substituted β-nitro ketones, a strategic class of compounds, under solid heterogeneous palladium catalysis and in the presence of triethylsilane is presented.
Key words
aliphatic nitro compounds - heterogeneous catalysis - reduction - synthetic methods - sustainable chemistrySupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588993.
- Supporting Information
-
References
- 1a Ono N. The Nitro Group in Organic Synthesis . Wiley-VCH; Weinheim: 2001
- 1b Ballini R. Bosica G. Fiorini D. Palmieri A. Petrini M. Chem. Rev. 2005; 105: 933
- 1c Sukhorukov AY. Sukhanova AA. Zlotin SG. Tetrahedron 2016; 72: 6191
- 2 Carr JB. Durham HG. Hass DK. J. Med. Chem. 1977; 20: 934
- 3 Ballini R. Gabrielli S. Palmieri A. Petrini M. Adv. Synth. Catal. 2010; 352: 2459
- 4 Palmieri A. Gabrielli S. Ballini R. Chem. Commun. 2010; 46: 6165
- 5 Li C.-S. Lacasse E. Tetrahedron Lett. 2002; 43: 3565
- 6a Onu N. Fujii M. Kaji A. Synthesis 1987; 532
- 6b Rosini G. Ballini R. Sorrenti P. Tetrahedron 1983; 39: 4127
- 7a Arai N. Narasaka K. Chem. Lett. 1995; 987
- 7b Arai N. Narasaka K. Bull. Chem. Soc. Jpn. 1997; 70: 2525
- 8 Kunetsky RA. Dilman AD. Tsvaygboym KP. Ioffe SL. Strelenko YA. Tartakovsky VA. Synthesis 2003; 1339
- 9a Just G. Crosilla D. Can. J. Chem. 1980; 58: 2349
- 9b Ballini R. Barboni L. Giarlo G. J. Org. Chem. 2004; 69: 6907
- 10a Miyakoshi T. Saito S. Kumanotani J. Chem. Lett. 1981; 1677
- 10b Gabrielli S. Palmieri A. Perosa A. Selva M. Ballini R. Green Chem. 2011; 13: 2026
- 11a Ballini R. Fiorini D. Gil MV. Palmieri A. Green Chem. 2003; 5: 475
- 11b Ballini R. Bosica G. Fiorini D. Palmieri A. Green Chem. 2005; 7: 825
- 11c Ballini R. Bosica G. Palmieri A. Pizzo F. Vaccaro L. Green Chem. 2008; 10: 541
- 11d Palmieri A. Gabrielli S. Ballini R. Green Chem. 2013; 15: 2344
- 11e Palmieri A. Gabrielli S. Sampaolesi S. Ballini R. RSC Adv. 2015; 5: 36652
- 12a Yu J.-Q. Wu H.-C. Ramarao C. Spencer JB. Ley SV. Chem. Commun. 2003; 678
- 12b Ley SV. Mitchell C. Pears D. Ramarao C. Yu J.-Q. Zhou W. Org. Lett. 2003; 5: 4665
- 12c Ley SV. Stewart-Liddon AJ. P. Pears D. Perni RH. Treacher K. Beilstein J. Org. Chem. 2006; 2: No. 15
- 13 Sheldon RA. Green Chem. 2007; 9: 1273
- 14a Capello C. Fischer U. Hungerbühler K. Green Chem. 2007; 9: 927
- 14b Alfonsi K. Colberg J. Dunn PJ. Fevig T. Jennings S. Johnson TA. Kleine HP. Knight C. Nagy MA. Perry DA. Stefaniak M. Green Chem. 2008; 10: 31
- 14c Dunn PJ. Chem. Soc. Rev. 2012; 41: 1452
- 14d Pace V. Hoyos P. Castoldi L. Domínguez de María P. Alcántara AR. ChemSusChem 2012; 5: 1369
- 14e Monticelli S. Castoldi L. Murgia I. Senatore R. Mazzeo E. Wackerlig J. Urban E. Langer T. Pace V. Monatsh. Chem. 2017; 148: 37
- 15 Ballini R. Fiorini D. Palmieri A. Tetrahedron Lett. 2004; 45: 7027
- 16 Products 1d, 1h, 1i and 1j were synthesized using a 1:1 mixture (3 mL/mmol) of MeOH and 2-MeTHF.
For application of Pd(0) EnCatTM 30NP in organic synthesis, see: