Non-covalent Li···H interaction in the synthesis of peri-disubstituted naphthalene proton sponges.
2019
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.
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