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2.1.2.1.4.1 Aryl Iodides

DOI: 10.1055/sos-SD-208-00078

Hay, M. B.; Hicks, J. D.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132165.

The palladium-catalyzed amination of aryl iodides by secondary heteroaromatic amines has been demonstrated using palladium catalysis, although published examples are limited to N-methylpyridinamine-derived nucleophiles. Buchwald and co-workers have disclosed a catalyst system comprised of the BrettPhos-based precatalyst 6/RuPhos (16) in the presence of cesium carbonate in tert-butyl alcohol that effects the amination of N-methylpyridin-2-amine (78) with 4-iodobenzonitrile (79) to give tertiary amine 80 (Scheme 62).[‌51‌] This system typically performs well for a variety of secondary aromatic amine aminations.[‌51‌]

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