Solvent-controlled leaving-group selectivity in aromatic nucleophilic substitution

L Hintermann, R Masuo, K Suzuki

Index: Hintermann, Lukas; Masuo, Ritsuki; Suzuki, Keisuke Organic Letters, 2008 , vol. 10, # 21 p. 4859 - 4862

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Citation Number: 32

Abstract

A solvent-controlled inversion of leaving group ability allows selective access to either of two internal substitution products in SNAr reactions of substrates with competing leaving groups. Application of this principle in a selective synthesis of the highly functionalized xanthone core of the antibiotic FD-594 is presented.