Broad Functionalization of DeepCavity Cavitands by Directed orthoMetalation

The endo and exorim positions of deepcavity cavitand 1were functionalized by directed orthometalation DoM procedures. A range of electrophilic quenchers led to hosts with ester, phenol and thioether functionality. In each case, a combination of host preorganization and reaction control resulted in far fewer products than the theoretical sixtynine. In addition to the nature of the lithiate, functionalization patterns were also dependent on the electrophile, with a general trend that the noncarbon electrophiles examined gave higher degrees of substitution. © WileyVCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008