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DOI: 10.1055/a-2644-2500
The Transformation of Alkyl- and Aryl-Sodium Reagents with Simple Amides for the Direct Synthesis of Ketones

Dedication
Dedicated to Prof. Paul Knochel with highest respect and ultimate gratitude.
Abstract
The transformation of alkyl and aryl sodium reagents with N-alkyl amides is described. The reaction sequence is initiated by an alkyl sodium reagent, which is generated in a flow reactor. The alkyl sodium reagent is either directly reacted with N-alkyl amides or used for the reaction with alkyl-substituted or alkoxy-substituted arenes to generate secondary sodium reagents which were then reacted with the amides to afford the desired ketones in moderate to good yields.
Publikationsverlauf
Eingereicht: 01. Juni 2025
Angenommen nach Revision: 26. Juni 2025
Artikel online veröffentlicht:
13. August 2025
© 2025. Thieme. All rights reserved.
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References
- 1a Anderson DE, Tortajada E, Hevia E. Angew Chem Int Ed 2023; 62: e202218498
- 1b Weinreb SM, Nahm S. Tetrahedron Lett 1981; 22: 3815
- 1c Khalid M, Mohammed S, Kalo A, Oriental J. Chem 2020; 36: 206
- 1d Senatore R, Ielo L, Monticelli S, Castoldi L, Pace V. Synthesis 2019; 51: 2792
- 1e Rajamanickam KR, Sirvin Rajan RP, Pootheri N, Chin-Fa Lee C-F, Lee S. Eur J Org Chem 2025; e202500210
- 1f Tortajada A, Anderson DE, Hevia E. Helv Chim Acta 2022; 105: e202200060
- 1g Bole LJ, Tortajada A, Hevia E. Angew Chem Int Ed 2022; 61: e202204262
- 1h Davison N, McMullin CL, Zhang L. et al. J Am Chem Soc 2023; 145: 6562
- 1i Anderson DE, Tortajada A, Hevia E. Angew Chem Int Ed 2024; 63: e202313556
- 1j Asako S, Takahashi I, Nakajima H, Ilies L, Takai K. Commun Chem 2021; 4: 76
- 1k Asako S, Nakajima H, Takai K. Nat Catal 2019; 2: 297
- 1l Ogi U, Ikeda S, Okano K, Horie M, Mori A. Chem Eur J 2025; 31: e202500355
- 1m Takahashi I, Tortajada A, Anderson DE, Ilies L, Hevia E, Asako S. Nat Synth. 2025
- 2 Knupe-Wolfgang P, Mahn B, Hilt G. Org Lett 2024; 26: 6972
- 3a Harenberg JH, Annapureddy RR, Karaghiosoff K, Knochel P. Angew Chem Int Ed 2022; 61: e202203807
- 3b Harenberg JH, Weidmann N, Wiegand AJ, Hoefer CA, Annapureddy RR, Knochel P. Angew Chem Int Ed 2021; 60: 14296
- 3c Harenberg JH, Weidmann N, Karaghiosoff K, Knochel P. Angew Chem Int Ed 2021; 60: 731
- 4 Weidmann N, Ketels M, Knochel P. Angew Chem Int Ed 2018; 57: 10748
- 5 Fuentes de Arriba ÁL, Lenci E, Sonawane M, Formery O, Dixon DJ. Angew Chem Int Ed 2017; 56: 3655
- 6 Tzaras D-I, Gorai M, Jacquemin T. et al. J Am Chem Soc 1867; 2025: 147
- 7 Nikitas NF, Apostolopoulou MK, Skolia E, Tsoukaki A, Kokotos CG. Chemistry 2021; 27: 7915
- 8a Law KR, McErlean CS. Tetrahedron Lett 2016; 57: 3113
- 8b Bie F, Liu X, Cao H. et al. Org Lett 2021; 23: 8098
- 9 Marcos-Atanes D, Vidal C, Navo CD, Peccati F, Jiménez-Osés G, Mascareñas JL. Angew Chem Int Ed 2023; 62: e20221451
- 10 Maiti S, Roy S, Ghosh P, Kasera A, Maiti D. Angew Chem Int Ed 2022; 61: e202207472
- 11 Clayden J, Watson DW, Chambers M. Tetrahedron 2005; 61: 3195
- 12 Bannwart L, Abele S, Tortoioli S. Synthesis 2016; 48: 2069
- 13 Tung TT, Nielsen J. Org Biomol Chem 2021; 19: 10073
For the initial report of Weinreb amides, see:
For recent reviews, see:
For additional reports on the synthesis of organo sodium reagents, see: