Dearomatization is a technique that has been steadily gaining interest in the fields of natural product synthesis and medicinal chemistry due to its potential to access structurally complex molecules from cheap, readily available aromatic precursors. A method for carrying out these dearomative processes is by coordination of aromatic molecules to a transition metal complex. Dihapto-coordination of aromatic molecules to an electron-rich metal fragment leads to a disruption of aromaticity due to the donation of electron density from the dπ-orbitals of the metal to the π*-orbitals of the arene. Such coordination allows for subsequent functionalizations to be performed on the uncoordinated π-bonds of the aromatic. Dihapto-coordination of anisole to an electron-rich tungsten fragment allows for two sequential protonations to generate a dicationic species capable of participating in electrophilic aromatic substitution reactions with a wide variety of aromatic molecules. The resulting species is a tungsten-stabilized oxocarbenium ion, which can be further elaborated into diverse organics such as allyl ethers, disubstituted cyclohexenes, and polycyclic compounds—all with remarkable stereocontrol of the final product.

Dearomative transformations of anisole via its dihapto-coordination to an electron-rich tungsten fragment

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