We report a six step synthesis of 2,6-bis(diethylaminomethyl)-4-pyridonate, a tridentate pyridonate ligand which we anticipate will promote C-H bond activation at platinum group metals due to its strong pi �basicity, as suggested by preliminary DFT calculations.  A double Claisen condensation of diethyl oxalate followed by an ammonia cyclization resulted in diethyl chelidamate.  The phenol group is then protected by methylation with iodomethane and then the two ethyl ester groups are reduced to hydroxymethyl groups by sodium borohydride in a THF-methanol mixture. The resulting diol is then tosylated and diethyl amine groups are added via nucleophilic substitution.

Synthesis of a pi-basic ligand for C-H bond activation

247th National Meeting (2014)

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