Pyridines are popular targets for synthetic chemists primarily because of their diverse and potent biological and  pharmacological activities.  We have recently displayed that N-propargylic �-enaminones 1  produce 4-iodopyridine derivatives 2  upon electrophilic cyclization with molecular iodine. Subsequently, in the present study, we have investigated the Pd-catalyzed Sonogashira and Suzuki-Miyaura couplings of 4-iodopyridines 2  with terminal alkynes and boronic acids, respectively, yielding a variety of highly substituted pyridines 3  and 4  in good to excellent yields. The scope and limitations of these reactions will be discussed.

Synthesis of highly substituted pyridines by Pd-catalyzed Sonogashira and Suzuki-Miyaura couplings of 4-iodopyridines

243rd National Meeting (2012)

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