Discovering new pharmaceuticals relies on chemical methods that can functionalize electron-deficient aromatic heterocycles. These entities are some of the most widespread chemical motifs found in drug compounds. Six-membered ring variants, such as pyridines and diazines, are particularly prominent, however, chemical methods that transform these heterocycles into a wide range of valuable derivatives are underdeveloped. This talk will outline a remarkably simple process to functionalize these heterocycles by converting them into phosphonium salts. The unique reactivity of the phosphonium ion will be exploited to form C–C, C–O, C–N, C–S and C–Halogen bonds and enable access to pharmaceutically relevant compounds. These methods will form functionalized derivatives in two chemical steps rather than four or five steps using conventional chemistry. The chemistry can be used as a tool for late-stage functionalization of complex structures to find more potent analogs.

Selective functionalization of pyridines and diazines via heterocyclic phosphonium salts

253rd National Meeting (2017)

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