N-Cumyl benzamide, sulfonamide, and aryl O-carbamate directed metalation groups. Mild hydrolytic lability for facile manipulation of directed ortho metalation derived aromatics

[GRAPHICS] N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds unde rgo directed ortho metalation under standard conditions to give, after quen ch 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 pro tocol for these new cumyl directed metalation groups (DMGs) suggests that t hey will supersede previous corresponding groups for synthetic anionic arom atic chemistry.