Heterocyclic arynes have long been investigated as useful intermediates for the preparation of functionalized heterocycles. However, the lack of regiocontrol has hindered the use of many of these species. Using the Aryne Distortion Model one can now predict the preferred site of attack on various hetarynes, as well as the general level of regioselectivity. Additionally, it is possible to design hetarynes that react with high levels of regioselectivity through the use of neighboring substituents. This presentation will describe our efforts in this regard, and will feature studies of 3,4-pyridyne. Using substituted variants, 3,4-pyridynes can undergo regioselective reaction at either terminus of the aryne to give various di- or trisubstituted pyridine derivatives. Furthermore, the directing group can be subsequently elaborated using transition metal catalysis to provide many unique substituted pyridine scaffolds.

Heterocyclic arynes: From computational design to synthetic applications

246th National Meeting (2013)

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