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15.1.1.1.7.1.4.7 Variation 7: Palladium-Catalyzed Iminoannulation of Alkynes

DOI: 10.1055/sos-SD-015-00002

Spitzner, D.Science of Synthesis, (20051553.

Palladium-catalyzed iminoannulation of alkynes gives pyridines, e.g. 168 (Scheme 58),[‌245‌] or annulated pyridines in good yields. The mechanism proposed for this iminoannulation entails oxidative addition at the vinylic iodide of the imine, e.g. 167, to the palladium(0) species to produce an organopalladium intermediate, which then inserts the acetylene producing a vinylic palladium intermediate, which then reacts with the imine to form a seven-membered palladacyclic ammonium salt. Reductive elimination, regeneration of palladium(0), and fragmentation of the tert-butyl group lead to the pyridine.[‌246‌,‌247‌]

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