Pd-Catalyzed Intramolecular C–N Bond Cleavage, 1,4-Migration, sp3 C–H Activation, and Heck Reaction: Four Controllable Diverse Pathways Depending on the Judicious Choice of the Base and Ligand
Journal of the American Chemical Society2014Vol. 137(3), pp. 1341–1347
Citations Over TimeTop 10% of 2014 papers
Abstract
Diverse and controllable pathways induced by palladium-catalyzed intramolecular Heck reaction of N-vinylacetamides for the synthesis of nitrogen-containing products in reasonable to high yields via tuning the phosphine ligands and bases are reported. Domino reactions including unique β-N-Pd elimination, 1,4-Pd migration, or direct acyl C-H bond functionalization were found to be involved forming different products, respectively. Given the ability of using the same starting material to generate diverse products via completely different chemoselective processes, these current methodologies offer straightforward access to valuable nitrogen-containing products under mild reaction conditions as well as inspire the discovery of novel reactions.
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