A new synthesis of substituted acridines is achieved by palladium-catalyzed addition of terminal acetylenes between the aryl rings of bis(2-bromophenyl)amine. By including a diamine base and elevating the temperature, the reaction pathway favors the formation of acridine over a double Sonogashira reaction to form bis(tolan)amine. This method is demonstrated with several aryl-alkynes and alkyl-alkynes.
Through a combined computational and isotopic labeling study, it has been observed that the activation energy for the aryl–alkyne ring closure of the azaborine containing 4-ethynyl-4a-aza-4b-boraphenanthrene is dramatically lower, and it appears to proceed via an alternate mechanism than that of its hydrocarbon analog. This catalyst-free reaction proceeds at modest reaction conditions compared with traditional pyrolytic synthetic methods and holds promise for the efficient construction of fused ring systems containing azaborine functional groups that may not be accessible in the purely hydrocarbon form.
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