Science of Synthesis

Hay, M. B.; Hicks, J. D., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 168.

The catalytic amination of aryl chlorides by secondary heteroaromatic amines has been demonstrated using palladium catalysis, although published examples are limited to N-methylpyridinamine-derived nucleophiles (‌Scheme 66‌). Buchwald and co-workers have shown that RuPhos-based precatalyst ‌43‌ in the presence of sodium tert-butoxide/tetrahydrofuran effects the amination of N-methylpyridin-4-amine (‌81‌) with chlorobenzene to give tertiary amine ‌86‌ in synthetically useful yields.[‌39‌] Although this catalyst system has not been extensively studied for couplings of secondary heteroaromatic amines with aryl chlorides, it has been applied in numerous examples where secondary aromatic/heteroaromatic amines are coupled with hetaryl chlorides.[‌39‌]

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References