Organic Letters

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

C Metallinos, S Nerdinger, V Snieckus

Index: Metallinos, Costa; Nerdinger, Sven; Snieckus, Victor Organic Letters, 1999 , vol. 1, # 8 p. 1183 - 1186

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Citation Number: 76

Abstract

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 ...