Improved Synthesis of Monohalogenated Cavitands and Their Use in the Synthesis of Further Functionalized Cavitands

Abstract

A new procedure for the synthesis of monohalogenated cavitands was established, which is at least one step shorter and far more atom-efficient than previously published pathways. These monohalogenated cavitands were demonstrated to be versatile synthons for the synthesis of further functionalized derivatives through cyanation, carboxylation, and a series of palladium-catalyzed Suzuki reactions.

Key words

cavitands - monofunctionalization - cross-coupling reactions

References

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8

In our first attempt, we used 1.5 equivalents of phenyllithium and iodine but only found traces of monoiodocavitand 3. A stepwise increase in the amount of phenyllithium to a 20:1 ratio did not lead to satisfying results; maximum yield by this procedure was 12% using phenyllithium/cavitand in a 2:1 ratio.