The Suzuki-Miyaura cross-coupling (SMC) of heteroaryl halides is particularly useful in pharmaceutical industry as heterocycles are widely present in many active pharmaceutical ingredients and natural products. In medicinal chemistry, the SMC of heteroaryl halides enables reaction sequence versatility as well as parallel synthesis. Instead of preparing numerous, diversified acyclic precursors prior to cyclization to make the corresponding heterocyles, the heterocyclic frameworks can be introduced as a whole into the complex target molecule by direct coupling, using SMC reaction. To date, unprotected nitrogen-rich heterocycles are well-recognized as a class of challenging substrates for SMC reactions, because they not only contain free NH groups,but also can deactivate the transition metal catalyst via complexation to the metal. To address this challenge, we have developed an improved palladium-catalyzed SMC reaction which is amenable to unprotected nitrogen-rich heterocycles.

Palladium-catalyzed Suzuki-Miyaura coupling reaction of unprotected nitrogen-rich heteroaryl halide

248th National Meeting (2014)

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