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
Synthesis 2019; 51(13): 2667-2677
DOI: 10.1055/s-0037-1611788
DOI: 10.1055/s-0037-1611788
special topic
Hitchhiker’s Guide to Reductive Amination
This work was supported by the RFBR (grant numbers 18-33-20065, 18-03-00839) and the Council of the President of the Russian Federation (Grant for Young Scientists No. MK- 1736.2019.3). D.C. is grateful to the generous support of RUDN "5-100" program.Weitere Informationen
Publikationsverlauf
Received: 14. Februar 2019
Accepted after revision: 12. März 2019
Publikationsdatum:
17. April 2019 (online)
Published as part of the Special Topic Amination Reactions in Organic Synthesis
Abstract
A comparative study of various widely used methods of reductive amination is reported. Specifically, such reducing agents as H2, Pd/C, hydride reagents [NaBH4, NaBH3CN, NaBH(OAc)3], and CO/Rh2(OAc)4 system were considered. For understanding the selectivity and activity of the reducing agents reviewed herein, different classes of starting materials were tested, including aliphatic and aromatic amines, as well as aliphatic and aromatic aldehydes and ketones. Most important advantages and drawbacks of the methods, such as selectivity of the target amine formation and toxicity of the reducing agents were compared. Methods were also considered from the viewpoint of green chemistry.
Key words
reductive amination - selectivity - atom efficiency - borohydride - hydrogen - palladium - carbon monoxideSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611788.
- Supporting Information
-
References
- 1 Robichaud A, Ajjou AN. Tetrahedron Lett. 2006; 47: 3633
- 2 Tripathi RP, Verma SS, Pandey J, Tiwari VK. Current Org. Chem. 2008; 12: 1093
- 3 Burke SD, Danheiser RL. Oxidizing and Reducing Agents . John Wiley & Sons; Hoboken: 1999
- 4 Baxter EW, Reitz AB. Org. React. 2001; 59: 1
- 5 Borch RF, Berstein MD, Durst HD. J. Am. Chem. Soc. 1971; 93: 2897
- 6 Ambrosi A, Denmark SE. Angew. Chem. Int. Ed. 2016; 26: 12164
- 7 Chusov D, List B. Angew. Chem. Int. Ed. 2014; 53: 5199
- 8 Afanasyev OI, Tsygankov AA, Usanov DL, Perekalin DS, Shvydkiy NV, Maleev VI, Kudinov AR, Chusov D. ACS Catal. 2016; 6: 2043
- 9 Clayden J, Greeves N, Warren S. Organic Chemistry, 2nd ed. Oxford University Press; Oxford: 2012: 234
- 10 Trost BM. Angew. Chem. Int. Ed. 1995; 34: 259
- 11 Ishioka M, Okada T, Matsuatma K. Carbon 1992; 30: 975
- 12 Jiang S, Wu Y, Zhang G, Li Y, Zhang D, Li K, Zhao G. Patent EP2657215A1, 2013: 7.
- 13 Abdel-Magid AF, Mehrman SJ. Org. Process Res. Dev. 2006; 10: 971
- 14 Hutchins RO, Natale NR. Org. Prep. Proced. Int. 1979; 11: 201
- 15 Gomez S, Peters JA, Maschmeyer T. Adv. Synth. Catal. 2002; 344: 1037
- 16 Lui N, Morandi WA, Müller TN. Patent WO 2012059585, 2012: 8.
- 17 Xie H, Li Y, Bai C, Wang R, Liu C, Hao C, Lin B, Cheng M, Zhao D. Bioorg. Med. Chem. 2016; 24: 1811
- 18 Markworth CJ, Marron BE, Swain NA. Patent WO 2010035166, 2010: 66.
- 19 Mandal AK, Ranbhan KJ, Saxena S, Gaikwad SR, Sarjekar PB. Patent WO 2013011518, 2013: 43.
- 20 Chen X, Dai K, Duquette J, Gribble MW, Huard JJr, Keegan KS, Li Z, Lively SE, Mcgee LR, Ragains ML, Wang X. Patent WO 2012129344, 2012: 130.
- 21 Magano J, Kiser EJ, Shine RJ, Chen MH. Org. Synth. 2013; 90: 74
- 22 Mistry DN, Soni KS, Vasoya SL, Kansal VK. Patent WO 2006003677, 2006: 19.
- 23 Fitzgerald RN, Millar A, Toczko JF. Patent WO 2012098075, 2012: 8.
- 24 Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. J. Org. Chem. 1996; 61: 3849
- 25 Elings JA, Furrer SM, Kaouas A, Winkel C. Patent US 2016295903, 2016: 5.
- 26 Bridger G, Skerlj R, Kaller A, Harwig C, Boguvki D, Wilson TR, Crawford J, McEachern EJ, Atsma B, Nan S, Zhou Y, Schols D. Patent US6750348, 2004: 73.
- 27 Bhattacharyya S. J. Org. Chem. 1995; 60: 4928
- 28 Welch WM, Kraska AR, Sarges R, Koe BK. J. Med. Chem. 1984; 27: 1508
- 29 Dismore CJ, Bergman JM. J. Org. Chem. 1998; 63: 4131
- 30 Coe JW, Vetelino MG, Bradlee MJ. Tetrahedron Lett. 1996; 37: 6045
- 31 Fukuyama T, Cheung M, Jow C.-K, Hidai Y, Kan T. Tetrahedron Lett. 1997; 38: 5831
- 32 Taber GP, Pfisterer DM, Colberg JC. Org. Process Res. Dev. 2004; 8: 385
- 33 Fei M, Sui D, Qi Z, Fan H, Chen R, Huang J. RSC Adv. 2016; 6: 94068
- 34 Wu J, Lu S, Gu H. RSC Adv. 2015; 5: 81395
- 35 Alinezhad H, Tajbakhsh M, Zare M. Synth. Commun. 2009; 39: 2907
- 36 Hamadi H, Javadi S. J. Chem. Sci. 2017; 129: 75
- 37 Alinezhad H, Tajbakhsh M, Hamidi N. Chin. Chem, Lett. 2010; 21: 47
- 38 Tajbakhsh M, Hosseinzadeh R, Alinezhad H, Ghahari S, Heydari A, Khaksar S. Synthesis 2011; 490
- 39 Reddy PS, Kanjilal S, Prasad SS, Prasad RB. N. Tetrahedron Lett. 2007; 48: 8807
- 40 Clark RB, He M, Deng Y, Sun C, Chen C.-L, Hunt DK, O’Brien WJ, Fyfe C, Grossman TH, Sutcliff JA, Xiao X.-Y. J. Med. Chem. 2013; 56: 8112
- 41 Yagafarov NZ, Usanov DL, Moskovets AP, Kagramanov ND, Maleev VI, Chusov D. ChemCatChem 2015; 7: 2590
- 42 Kuchuk EA, Muratov K, Perekalin DS, Chusov D. Org. Biomol. Chem. 2019; 17: 83
- 43 Kolesnikov PN, Yagafarov NZ, Usanov DL, Maleev VI, Chusov D. Org. Lett. 2015; 17: 173
- 44 Kikugawa Y, Kuramoto M, Saito L, Yamada S. Chem. Pharm. Bull. 1973; 21: 1927
- 45 Andraos J. Green Chemistry Metrics . John Wiley & Sons; Hoboken: 2009: 69