In alliance with tertiary amines, TiCl 4 is well-known to mediate aldol type condensation reactions 1 and oxidative coupling of certain ester enolates. 2 Recently, it was observed in this laboratory that the TiCl 4 /Et 3 N reagent system is useful for the oxidative coupling of aryl methyl ketimines to 2,5-diarylpyrroles 3a and for the direct metalation of 1-alkynes. 3b Also, it was observed that trialkylamines are oxidized to iminium ions by TiCl 4 with concomitant formation of TiCl 3 . 4a,b Herein we report that the reaction of TiCl 4 with N,N-dialkylanilines gives the corresponding N,N,N′,N′-tetraalkylbenzidines (eq 1).
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