N-Cumyl Benzamide, Sulfonamide, and Aryl O-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics

N -Cumyl benzamide ( 2 ), sulfonamide ( 8 ), and O -carbamate ( 11 ) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides ( 7 ), 1,2-benzisothiazole 1,1-dioxides ( 10b ), and ortho-substituted phenols ( 13a ) and salicylamides ( 13b ) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.