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The metalation of an amine by a lithium alkoxide in protic medium possibly proceeds by the two-step six-center deprotonation–lithiation mechanism sketched below. Evidence for this reaction pathway comes from the X-ray structure analysis of [Li(tBuOH)2(thf)2][cb] (Hcb = carbazole), which exhibits a disordered proton between a carbazole N atom and an O atom of a tBuOH molecule. This compound thus provides a model for the precurser complex 1 and the product complex 2 of the deprotonation. The subsequent rearrangement of 2 to 3 could occur stepwise rather than by a converted mechanism.
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Lambert et al. (1992) studied this question.
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