Efficient Synthesis of Bis(4-Dimethaminophenyl)arylmethanes and Bis(4-Diamethaminophenyl)alkanes Using Iodine Reagent

Abstract

A novel synthetic utility of NaICl₂ for the preparation of bis(4-dimethaminophenyl)arylmethanes and bis(4-dimethaminophenyl)alkanes is described. In the presence of an aqueous solution of NaICl₂, the reaction of arenes with aromatic aldehydes gives corresponding triarylmethane derivatives regioselectively in moderate to good yields. The method is also useful for the preparation of diarylalkane derivatives by using aliphatic aldehydes.

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GRAPHICAL ABSTRACT

Keywords:

• Bis(4-dimethaminophenyl)alkanes
• bis(4-dimethaminophenyl)arylmethane
• carbon–carbon coupling
• sodium dichloroiodate

ACKNOWLEDGMENT

V. N. T. thanks the Institute of Chemical Technology, Mumbai (ICT), for providing financial support under the Golden Jubilee Fund.

Notes

^a Reaction was conducted in acetonitrile and aqueous NaICl₂ at room temperature.

^b Isolated yield of 4,4′-(phenylmethylene)bis(N,N-dimethylaniline) after column chromatography.

^a Reaction conditions: N,N′-dimethylaniline (2 equiv), NaICl₂ (2 equiv), and aldehyde (1 equiv) in acetonitrile.

^b Isolated yields after column chromatography and structures were confirmed by comparison of IR, ¹H NMR, and mp with literature reports.

^c Reflux temperature.