Pyridylic anions are soft nucleophiles in the palladium-catalyzed C(sp3)-H allylation of 4-alkylpyridines
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Wasfy, Nour
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York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Wasfy, Nour
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Rasheed, Faizan
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York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Rasheed, Faizan
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Robidas, Raphael
[2
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Hunter, Isabelle
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York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Hunter, Isabelle
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Shi, Jiaqi
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York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Shi, Jiaqi
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Doan, Brian
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York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Doan, Brian
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Legault, Claude Y.
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Univ Sherbrooke, Dept Chem, Ctr Green Chem & Catalysis, 2500 Blvd Univ, Sherbrooke, PQ J1K 2R1, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Legault, Claude Y.
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Fishlock, Dan
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F Hoffmann La Roche Ltd, Proc Chem & Catalysis, Synthet Mol Tech Dev, CH-4070 Basel, SwitzerlandYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Fishlock, Dan
[3
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Orellana, Arturo
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York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, CanadaYork Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
Orellana, Arturo
[1
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[1] York Univ, Dept Chem, 4700 Keele St, N York, ON M3J 1P3, Canada
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.