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   Devkota, Govinda Prasad; Carson, William P.; Hartley, C. Scott (February 2023, The Journal of Organic Chemistry)
2. A predictive journey towards trans -thioamides/amides

   https://doi.org/10.1039/D2CC04228B  

   Tomasini, Michele; Zhang, Jin; Zhao, Hui; Besalú, Emili; Falivene, Laura; Caporaso, Lucia; Szostak, Michal; Poater, Albert (September 2022, Chemical Communications)

   The cis – trans isomerization of (thio)amides was studied by DFT calculations to get the model for the higher preference for the cis conformation by guided predictive chemistry, suggesting how to select the alkyl/aryl substituents on the C/N atoms that lead to the trans isomer. Multilinear analysis, together with cross-validation analysis, helped to select the best fitting parameters to achieve the energy barriers of the cis to trans interconversion, as well as the relative stability between both isomers. Double experimental check led to the synthesis of the best trans candidate with sterically demanding t -butyl substituents, confirming the utility of predictive chemistry, bridging organic and computational chemistry. 

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4. Synthesis of biaryl ketones by arylation of Weinreb amides with functionalized Grignard reagents under thermodynamic control vs. kinetic control of N , N -Boc ₂ -amides

   https://doi.org/10.1039/d0ob00813c  

   Li, Guangchen; Szostak, Michal (May 2020, Organic & Biomolecular Chemistry)

   null (Ed.)

   A highly efficient method for chemoselective synthesis of biaryl ketones by arylation of Weinreb amides ( N -methoxy- N -methylamides) with functionalized Grignard reagents is reported. This protocol offers rapid entry to functionalized biaryl ketones after Mg/halide exchange with i-PrMgCl·LiCl under operationally-simple and practical reaction conditions. The scope of the method is highlighted in >40 examples, including bioactive compounds and pharmaceutical derivatives. Collectively, this transition-metal-free approach offers a major advantage over the recently established cross-coupling of amides by oxidative addition of N–C(O) bonds. Considering the utility of amide acylation reactions in modern synthesis, we expect that this method will be of broad interest. 

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5. Ligand-enabled ortho -C–H olefination of phenylacetic amides with unactivated alkenes

   https://doi.org/10.1039/c7sc04827k  

   Lu, Ming-Zhu; Chen, Xing-Rong; Xu, Hui; Dai, Hui-Xiong; Yu, Jin-Quan (January 2018, Chemical Science)

   Although chelation-assisted C–H olefination has been intensely investigated, Pd( ii )-catalyzed C–H olefination reactions are largely restricted to acrylates and styrenes. Here we report a quinoline-derived ligand that enables the Pd( ii )-catalyzed olefination of the C(sp 2 )–H bond with simple aliphatic alkenes using a weakly coordinating monodentate amide auxiliary. Oxygen is used as the terminal oxidant with catalytic copper as the co-oxidant. A variety of functional groups in the aliphatic alkenes are tolerated. Upon hydrogenation, the ortho -alkylated product can be accessed. The utility of this reaction is also demonstrated by the late-stage diversification of drug molecules. 

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