Six-membered aromatic rings are ubiquitous in natural products, drugs, and agrochemicals. Classical approaches to functionalize arenes involve electrophilic aromatic substitution (EAS) and nucleophilic aromatic substitution (S_NAr) reactions to install a single substituent directly on the carbon framework. However, pre-installed functional groups and electron-withdrawing substituents are required for successful functionalization with nucleophiles. In addition, EAS reactions are guided by pre-existing substituents on the arene ring. Electron-rich substituents guide these electrophilic processes to the ortho and para positions. Thus, a synthetic challenge arises for meta-selective nucleophilic functionalization of electron-rich arenes. I present an alternative method to achieve meta-selective functionalization directly from the C-H bond using a benzene dearomatization strategy mediated by row 6 transition metal complexes. Diels-Alder reactions from the dearomatized intermediate with alkynes will allow direct di-functionalization at the ortho and meta positions of these arenes. In addition, using nitriles, tetrahydropyridines, isocyanates, aryldiazonium salts, and imines as dienophiles in hetero-Diels-Alder reactions allows for transmutation of the benzene core into a variety of N-heterocycles.