Chemoselective Deprotonative Lithiation of Azobenzenes: Reactions and Mechanisms

…, AS Castanet, KPP Nguyen, J Mortier

Index: Nguyen, Thi-Huu; Chau, Nguyet Trang Thanh; Castanet, Anne-Sophie; Nguyen, Kim Phi Phung; Mortier, Jacques Organic Letters, 2005 , vol. 7, # 12 p. 2445 - 2448

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Citation Number: 4

Abstract

Whereas standard strong bases (n-BuLi, s-BuLi/TMEDA, n-BuLi/t-BuOK, TMPMgCl· LiCl, and LDA) reduce the N N bond of the parent azobenzene (Y= H), aromatic H→ Li permutation occurs with LTMP when a suitable director of lithiation (Y= OMe, CONEt2, F) is present in the benzene residue of the azo compound. The method allows direct access to new substituted azobenzenes.