The strongly pi-basic tridentate ligand (2,6-bis diethylaminomethyl)-gamma-pyridone (NN0(H)N) has been prepared in a seven step synthesis from acetone and diethyl oxalate, and the benzyl protected precursor reacts with NiCl2 to form (NN0(Bn)N)NiCl2, which has been crystallographically characterized. The gamma-oxide group is considerably more pi-donating than a gamma-dimethylamino group, and preliminary DFT studies suggest that this pincer ligand should be exceptionally good at promoting C-H oxidative addition at platinum group metal complexes of the form [(NN0N)M]+n (n = 0, 1). The importance of strong pi-donation and weak sigma-donation in the promotion of concerted oxidative addition to T-shaped 14e- fragments will be discussed.

Multistep synthesis of a tridentate pi-donating pyridone pincer designed to drive C-H oxidative addition

2019 Spring National Meeting

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