Synthesis 2020; 52(01): 98-104
DOI: 10.1055/s-0039-1690230
paper
© Georg Thieme Verlag Stuttgart · New York

Noncovalent Li···H Interaction in the Synthesis of peri-Disubstituted Naphthalene Proton Sponges

,
Artyom A. Yakubenko

This work was supported by the Russian Science Foundation (project 18-73-00020).
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Publikationsverlauf

Received: 05. September 2019

Accepted after revision: 05. Oktober 2019

Publikationsdatum:
24. Oktober 2019 (online)


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Abstract

Noncovalent Li···H interaction was utilised 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 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after quenching the reaction mass with different electrophiles.

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