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Synlett 2012(2): 317-318  
DOI: 10.1055/s-0031-1290127
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© Georg Thieme Verlag Stuttgart ˙ New York

Lithium Naphthalenide

Jian-Wu Gao*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
e-Mail: gjw1112003@yahoo.com.cn;
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Publication History

Publication Date:
04 January 2012 (online)

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Introduction

During the last three decades, the use of lithium naphthalenide (LN) as a reductant in organic synthesis has increased considerably. It has been used for the reductive cleavage of benzyl ethers, [¹] N,N,N′,N′-tetramethylphosphorodiamidates, [²] and chlorinated aryloxyalkanoic acids. [³] It was found to be a useful reagent for the removal of sulfide and sulfone. [4] In addition, LN-induced reductive ­decyanation, [5] alkylation, [6] and dehalogenation [7] are also readily accomplished.

Lithium naphthalenide can be dissolved in ether, benzene, and tetrahydrofuran, and can be stored in solution up to several days. But it must be protected from air and moisture and can react with protic solvents and tetrahydrofuran at elevated temperatures. [8] It can be conveniently prepared as a stable stock solution by mixing equal parts of freshly cut lithium metal and naphthalene in tetrahydrofuran at room temperature. [9]

Scheme 1

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