ArticleChemical science2020
Pyridylic anions are soft nucleophiles in the palladium-catalyzed C(sp
Article in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Deprotonation and Alkylation of Weakly Acidic C(spAngewandte Chemie (International ed. in English) · 2026Article
- Palladium-catalyzed allylation of 2- and 4-alkylpyridines via N-allyl alkylidene dihydropyridine intermediates.Tetrahedron letters · 2023Article
- Polar Heterobenzylic C(spJournal of the American Chemical Society · 2023Article
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Authors and funding
9 authors.
Funding
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Abstract
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 p
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