Palladium-assisted room-temperature nucleophilic substitution of an unactivated aryl fluoride

Adam Scharf; Israel Goldberg; Arkadi Vigalok

doi:10.1021/om201175d

Palladium-assisted room-temperature nucleophilic substitution of an unactivated aryl fluoride

Adam Scharf, Israel Goldberg, Arkadi Vigalok

School of Chemistry

Tel Aviv University

Research output: Contribution to journal › Article › peer-review

Abstract

An organometallic palladium(II) complex of an 8-fluoroquinoline-based chelating ligand undergoes very facile nucleophilic substitution of the "unactivated" fluorine atom with the methoxy group upon simple stirring of its THF solution with sodium methoxide at room temperature. The final product of this reaction lacks the aromaticity in the heterocyclic ring of the quinoline moiety which might play an important role in the overall reactivity.

Original language	English
Pages (from-to)	1275-1277
Number of pages	3
Journal	Organometallics
Volume	31
Issue number	4
DOIs	https://doi.org/10.1021/om201175d
State	Published - 27 Feb 2012

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om201175d

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abstract = "An organometallic palladium(II) complex of an 8-fluoroquinoline-based chelating ligand undergoes very facile nucleophilic substitution of the {"}unactivated{"} fluorine atom with the methoxy group upon simple stirring of its THF solution with sodium methoxide at room temperature. The final product of this reaction lacks the aromaticity in the heterocyclic ring of the quinoline moiety which might play an important role in the overall reactivity.",

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AU - Goldberg, Israel

AU - Vigalok, Arkadi

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N2 - An organometallic palladium(II) complex of an 8-fluoroquinoline-based chelating ligand undergoes very facile nucleophilic substitution of the "unactivated" fluorine atom with the methoxy group upon simple stirring of its THF solution with sodium methoxide at room temperature. The final product of this reaction lacks the aromaticity in the heterocyclic ring of the quinoline moiety which might play an important role in the overall reactivity.

AB - An organometallic palladium(II) complex of an 8-fluoroquinoline-based chelating ligand undergoes very facile nucleophilic substitution of the "unactivated" fluorine atom with the methoxy group upon simple stirring of its THF solution with sodium methoxide at room temperature. The final product of this reaction lacks the aromaticity in the heterocyclic ring of the quinoline moiety which might play an important role in the overall reactivity.

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DO - 10.1021/om201175d

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JO - Organometallics

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Palladium-assisted room-temperature nucleophilic substitution of an unactivated aryl fluoride

Abstract

All Science Journal Classification (ASJC) codes

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