Synthesis, Table of Contents Synthesis DOI: 10.1055/a-2644-2500 Paper Published as part of the Special Topic Dedicated to Prof. Paul Knochel The Transformation of Alkyl- and Aryl-Sodium Reagents with Simple Amides for the Direct Synthesis of Ketones Paula Knupe-Wolfgang 1 Institut für Chemie, Carl von Ossietzky Universität Oldenburg, Oldenburg, Germany , Gerhard Hilt 1 Institut für Chemie, Carl von Ossietzky Universität Oldenburg, Oldenburg, Germany › Author AffiliationsRecommend Article Abstract Buy Article All articles of this category 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. Keywords KeywordsAlkyl sodium - Alkylation - Amides - Ketones - Sodiation - Transsodiation Full Text References References 1a Anderson DE, Tortajada E, Hevia E. Angew Chem Int Ed 2023; 62: e202218498 For the initial report of Weinreb amides, see: 1b Weinreb SM, Nahm S. Tetrahedron Lett 1981; 22: 3815 For recent reviews, see: 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 For additional reports on the synthesis of organo sodium reagents, see: 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 Supplementary Material Supplementary Material Supplementary Material
