Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles

Eiji Yamamoto, Satoshi Ukigai, Hajime Ito

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A new reaction has been developed for the formal nucleophilic silyl substitution of aryl halides with silyllithium or silylpotassium reagents. Dimethylphenylsilyllithium reacted with various aryl halides to form the corresponding arylsilanes in moderate to good yields with concomitant formation of the disilanes under the optimized reaction conditions. Mechanistic studies indicated that this silyl substitution reaction progresses through polar halogenophilic attack of silyl nucleophiles.

Original languageEnglish
Pages (from-to)2460-2464
Number of pages5
JournalSynlett
Volume28
Issue number18
DOIs
Publication statusPublished - Nov 13 2017

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Nucleophiles
Substitution reactions

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles. / Yamamoto, Eiji; Ukigai, Satoshi; Ito, Hajime.

In: Synlett, Vol. 28, No. 18, 13.11.2017, p. 2460-2464.

Research output: Contribution to journalArticle

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