Abstract
AbstractAn asymmetrical, 9,10‐dihydroacridine‐based proligand, H[NNOtBu], featuring a diphenylamine and a tert‐butyl ether substituent on the 4 and 5 positions is reported. The ligand can be synthesized in a one‐pot, palladium‐catalysed reaction in reasonable yields from symmetrical starting materials. The coordination chemistry of this ligand has been investigated towards a range of main group metals. The reaction between the proligand H[NNOtBu] and benzyl potassium proceeded as expected, leading to deprotonation of the amine to give the potassium amide in good yields. In contrast, the reactions between H[NNOtBu] and MeMgBr or AlMe3 were found to be more complex, leading to both deprotonation of the amine and C−O bond cleavage of the ligand's tert‐butyl ether group. This C−O bond cleavage was found to be preventable when using the bulkier reagent n‐butyl‐sec‐butylmagnesium, yielding the monometallic complex [NNOtBu]MgsBu in good yields.
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