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1. Transamidation of N-acyl-glutarimides with amines

   Liu, Yongmei; Achtenhagen, Marcel; Liu, Ruzhang; Szostak, Michal (February 2018, Organic & biomolecular chemistry)

   The development of new transamidation reactions for the synthesis of amides is an important and active area of research due to the central role of amide linkage in various fields of chemistry. Herein, we report a new method for transamidation of N-acyl-glutarimides with amines under mild, metal-free conditions that relies on amide bond twist to weaken amidic resonance. A wide range of amines and functional groups, including electrophilic substituents that would be problematic in metal-catalyzed protocols, are tolerated under the reaction conditions. Mechanistic experiments implicate the amide bond twist, thermodynamic stability of the tetrahedral intermediate and leaving group ability of glutarimide as factors controlling the reactivity of this process. The method further establishes the synthetic utility of N-acyl-glutarimides as bench-stable, twist-perpendicular, amide-based reagents in acyl-transfer reactions by a metal-free pathway. The origin of reactivity of N-acyl-glutarimides in metal-free and metal-catalyzed processes is discussed and compared. 

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2. N -Acyl-Glutarimides: Privileged Scaffolds in Amide N-C Bond Cross-Coupling: N -Acyl-Glutarimides: Privileged Scaffolds in Amide N-C Bond Cross-Coupling

   https://doi.org/10.1002/ejoc.201800109  

   Meng, Guangrong; Szostak, Michal (June 2018, European Journal of Organic Chemistry)
3. N-Acyl-5,5-Dimethylhydantoins: Mild Acyl-Transfer Reagents for the Synthesis of Ketones using Pd–PEPPSI or Pd/Phosphine Catalysis

   https://doi.org/10.1021/acs.oprd.0c00054  

   Wang, Chang-An; Liu, Chengwei; Szostak, Michal (April 2020, Organic Process Research & Development)

   N-Acyl-hydantoins have emerged as novel acyl transfer reagents for the synthesis of ketones via selective N–C(O) cleavage. Herein, we report two new protocols for the cross-coupling of N-acyl-5,5-dimethylhydantoins using versatile and readily accessible Pd–PEPPSI or Pd/phosphine catalysts. The acyl Suzuki reactions afford biaryl ketones in good to excellent yields under operationally-simple conditions using commercially-available, bench- and air-stable twisted N-acyl-hydantoins as acyl donors. The method complements and expands on the previous protocol for the cross-coupling of N-acyl-hydantoins (Org. Process Res. Dev. 2018, 22, 1188). 

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4. Amide N–C Bond Activation: A Graphical Overview of Acyl and Decarbonylative Coupling

   https://doi.org/10.1055/a-2035-6733  

   Liu, Chengwei; Szostak, Michal (January 2023, SynOpen)

   Abstract This Graphical Review provides an overview of amide bond activation achieved by selective oxidative addition of the N–C(O) acyl bond to transition metals and nucleophilic acyl addition, resulting in acyl and decarbonylative coupling, together with key mechanistic details pertaining to amide bond distortion underlying this reactivity manifold. 

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5. Twisted N -Acyl-hydantoins: Rotationally Inverted Urea-Imides of Relevance in N–C(O) Cross-coupling

   https://doi.org/10.1021/acs.joc.8b02691  

   Szostak, Roman; Liu, Chengwei; Lalancette, Roger; Szostak, Michal (November 2018, The Journal of Organic Chemistry)