Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In an article, author is Wasfy, Nour, once mentioned the application of 220000-87-3, Name is 4-Chloro-N-methylpicolinamide, molecular formula is C7H7ClN2O, molecular weight is 170.6, MDL number is MFCD02185921, category is pyridine-derivatives. Now introduce a scientific discovery about this category, Application In Synthesis of 4-Chloro-N-methylpicolinamide.
Pyridylic anions are soft nucleophiles in the palladium-catalyzed C(sp(3))-H allylation of 4-alkylpyridines
We report a mild palladium-catalyzed method for the selective allylation of 4-alkylpyridines in which highly basic pyridylic anions behave as soft nucleophiles. This method exploits alkylidene dihydropyridines, which are semi-stable intermediates readily formed using a ‘soft-enolization’ approach, in a new mechanistic manifold for decarboxylative allylation. Notably, the catalytic generation of pyridylic anions results in a substantially broader functional group tolerance compared to other pyridine allylation methods. Experimental and theoretical mechanistic studies strongly suggest that pyridylic anions are indeed the active nucleophiles in these reactions, and that they participate in an outer-sphere reductive elimination step. This finding establishes a new pK(a) boundary of 35 for soft nucleophiles in transition metal-catalyzed allylations.
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Reference:
Pyridine – Wikipedia,
,Pyridine | C5H5N – PubChem