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 2025; 57(04): 732-739
DOI: 10.1055/a-2410-2291
DOI: 10.1055/a-2410-2291
feature
Platinum-Catalyzed Deoxygenation of N-Acyloxyamines
We gratefully acknowledge the National Research Foundation of Korea (NRF-2020R1A2C2009636 and RS-2024-00409659).

Abstract
We report a Pt-catalyzed double deoxygenative transformation of N-acyloxyamines, employing PtCl2 catalyst without external ligand under mild conditions. This method facilitates efficient C–N bond formation and can be used to synthesize a broad spectrum of alkylated secondary and tertiary amines with excellent yields. The adaptability and effectiveness of this approach highlight the potential of platinum catalysis to extend beyond traditional synthetic boundaries.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2410-2291.
- Supporting Information
Publication History
Received: 20 August 2024
Accepted after revision: 05 September 2024
Accepted Manuscript online:
05 September 2024
Article published online:
26 September 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Amines: Synthesis, Properties and Applications . Lawerence SA. Cambridge University; Cambridge: 2004
- 1b Industrial Organic Chemicals, 2nd ed. Wittcoff HA, Reuben BG, Plotkin JS. Wiley-Interscience; New York: 2004
- 2a Advanced Organic Chemistry, 5th ed. Smith MB, March J. Wiley-Interscience; New York: 2001
- 2b Modern Aminations Methods . Ricci A. Wiley-VCH; Weinheim: 2007
- 3a Breuer M, Ditrich K, Habicher T, Hauer B, Keßeler M, Stürmer R, Zelinski T. Angew. Chem. Int. Ed. 2004; 43: 788
- 3b Beauchemin AM, Moran J, Lebrun M.-E, Seguin C, Dimitrijevic E, Zhang L, Gorelsky SI. Angew. Chem. Int. Ed. 2008; 47: 1410
- 3c Mueller TE, Hultzsch KC, Yus M, Foubelo F, Tada M. Chem. Rev. 2008; 108: 3795
- 3d Guillena G, Ramon DJ, Yus M. Chem. Rev. 2010; 110: 1611
- 3e Bähn S, Imm S, Neubert L, Zhang M, Neumann H, Beller M. ChemCatChem 2011; 3: 1853
- 3f Collet F, Lescot C, Dauban P. Chem. Soc. Rev. 2011; 40: 1926
- 3g Ramirez TA, Zhao B, Shi Y. Chem. Soc. Rev. 2012; 41: 931
- 4a Kobayashi S, Ishitani H. Chem. Rev. 1999; 99: 1069
- 4b Nugent TC, El-Shazly M. Adv. Synth. Catal. 2010; 352: 753
- 4c Xie J.-H, Zhu S.-F, Zhou Q.-L. Chem. Rev. 2011; 111: 1713
- 4d Barrios-Rivera J, Xu Y, Wills M, Vyas VK. Org. Chem. Front. 2020; 7: 3312
- 5a Li B, Sortais J.-B, Darcel C. RSC Adv. 2016; 6: 57603
- 5b Khalimon AY, Gudun KA, Hayrapetyan D. Catalysts 2019; 9 490
- 5c Cabrero-Antonino JR, Adam R, Papa V, Beller M. Nat. Commun. 2020; 11: 3893
- 6a Padwa A, Bur SK. Tetrahedron 2007; 63: 5341
- 6b Padwa A. Chem. Soc. Rev. 2009; 38: 3072
- 6c Tietze LF, Kinzel T, Brazel CC. Acc. Chem. Res. 2009; 42: 367
- 7 Modak A, Maiti D. Org. Biomol. Chem. 2016; 14: 21
- 8a Magano J, Dunetz JR. Org. Process Res. Dev. 2012; 16: 1156
- 8b Werkmeister S, Junge K, Beller M. Org. Process Res. Dev. 2014; 18: 289
- 8c Pritchard J, Filonenko GA, Van Putten R, Hensen EJ, Pidko EA. Chem. Soc. Rev. 2015; 44: 3808
- 9a Lunde SA, Sydnes MO. Synlett 2013; 24: 2340
- 9b Gusak KN, Ignatovich ZV, Koroleva EV. Russ. Chem. Rev. 2015; 84: 288
- 9c Irrgang T, Kempe R. Chem. Rev. 2020; 120: 9583
- 10 Larson GL, Liberatore RJ. Org. Process Res. Dev. 2021; 25: 1719
- 11 Zhou S, Junge K, Addis D, Das S, Beller M. Angew. Chem. 2009; 121: 9671
- 12 Igarashi M, Fuchikami T. Tetrahedron Lett. 2001; 42: 1945
- 13 Dombray T, Helleu C, Darcel C, Sortais JB. Adv. Synth. Catal. 2013; 355: 3358
- 14 Simmons BJ, Hoffmann M, Hwang J, Jackl MK, Garg NK. Org. Lett. 2017; 19: 1910
- 15 Macaulay CM, Ogawa T, McDonald R, Sydora OL, Stradiotto M, Turculet L. Dalton Trans. 2019; 9581
- 16 Ali K, Cho EJ. Org. Lett. 2024; 26: 5192
For books, see:
For reviews, see:
For reviews on the catalytic reduction of imines, see:
For reviews on the catalytic reduction of amides, see:
For selected examples to show the benefits of domino or tandem catalytic processes, see:
For selected reviews on the catalytic reduction of carbonyl compounds, see:
For reviews on the catalytic reductive amination of carbonyl compounds, see: