Non-covalent Li···H interaction was utilized as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n-BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri-position and with up to 90% yield. A series of 4,5-disubstituted derivatives of DMAN has been prepared in a good to excellent yield after quenching the reaction mass with different electrophiles.
Keywords: Agostic interaction; metallation; proton sponge; lithium
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Antonov, A. S. Beilstein Arch. 2019, 201914. doi:10.3762/bxiv.2019.14.v1
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