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2.1.1.1.2 Palladium-Catalyzed Coupling of Alkylamines with Aryl and Alkenyl Halides

DOI: 10.1055/sos-SD-208-00002

Tomás-Gamasa, M.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013224.

Palladium-catalyzed coupling reactions have garnered enormous interest since the 1990s and nowadays are recognized as an excellent and usually superior alternative to copper catalysis for the C—N bond formation between alkylamines and aryl halides. In 1995, the groups of Buchwald and Hartwig reported the first practical palladium-catalyzed protocols for the coupling of aryl halides with amines using the sterically hindered tri-2-tolylphosphine as a ligand.[‌56‌,‌57‌] Since this discovery, great advances have been reached in this area, which have typically been driven by the implementation of new classes of mostly phosphorus-containing ligands.

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