It was observed that Pd(OAc)<sub>2</sub> catalyzed heterogeneous Suzuki couplings of relatively unreactive basic nitrogen-containing aryl chlorides with arylboronic acids in water in the absence of added base can be greatly activated by the addition of bulky triorganophosphine ligands. Good to high yields of products were obtained from a series of “base-free” aqueous Suzuki coupling reactions of a wide range of aryl chlorides containing aliphatic amine substituents and aminopyridines with several representative arylboronic acids. The observed pH changes of the aqueous phase during the coupling process indicate that the reaction takes place partially or entirely under acidic conditions. The control reactions conducted in various acidic buffers demonstrated that the basic nitrogen containing aryl halides could readily couple with arylboronic acids with an acidic aqueous solution.

Pd-catalyzed Suzuki coupling reactions of aryl chlorides containing basic nitrogen centers with arylboronic acids in water in the absence of added base

254th National Meeting (2017)

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