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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

Alexander S. Antonov  ∗
,
Artyom A. Yakubenko
This work was supported by the Russian Science Foundation (project 18-73-00020).
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Publication History

Received: 05 September 2019

Accepted after revision: 05 October 2019

Publication Date:
24 October 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.

Key words

agostic interaction - metalation - proton sponge - lithium - naphthalene

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690230.
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