The synthesis of a functionalized supramolecular cavitand with inwardly oriented AuI and P=O moieties was explored, including its catalytic proclivity in the selective hydration of internal alkynes. The cavitand works as a supramolecular flask device: AuI coordinates to the triple bond, the P=O moiety connects with a H2O molecule, and the cavity favors folding of a single alkynyl side chain. Several tests of different substrate patterns indicated that the cavity was substrate specific, similar to enzymatic catalysis.

A preparative synthesis of an inwardly oriented phosphoramidite-Au dinuclear resorcinarene cavitand complex is described, including a description of potent catalytic abilities. The cavitand structure was determined by crystallographic analysis, which revealed that the phosphoramidite P-N bonds point outside placing the two Au atoms inside. We explored the catalytic

The effect of a metallocatalytic cavity flanked by aromatic rings on the catalytic dimerization of terminal alkynes was explored through a comparison with model catalysts that weakened the cavity. The diquinoxaline‐spanned resorcin[4]arene provided a definite compartment, in which the two Au centers enticed two alkynes to undergo the coupling reaction. We synthesized two kinds of model compounds in which one lacked two quinoxaline walls and the other had two pyrazine walls and found that these catalysts exhibited much lower reactivity. The two quinoxaline moieties proved to be quintessential for the catalytic event.

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