Synthesis

Synthesis of halogenated phenols by directed ortho-lithiation and ipso-iododesilylation reactions of O-aryl N-isopropylcarbamates

M Kauch, D Hoppe

Index: Kauch, Matthias; Hoppe, Dieter Synthesis, 2006 , # 10 p. 1578 - 1589

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Citation Number: 14

Abstract

Abstract The regioselective synthesis of halogenated phenols via directed ortho-lithiation reactions of in situ N-silylated O-aryl N-isopropylcarbamates is reported. This protocol is complemented by ipso-iododesilylation reactions of C-silylated carbamates and iodine- magnesium exchange reactions, which are facilitated by the adjacent carbamoyl group. These methods provide an entry into a series of o-fluoro-, o-iodo-, and o, o′- ...