1,1′-Dialkynylferrocenes as Substrates for Bidirectional Alkyne Metathesis Reaction

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OriginalspracheEnglisch
Seiten (von - bis)4510-4518
Seitenumfang9
FachzeitschriftEuropean Journal of Organic Chemistry
Jahrgang2015
Ausgabenummer20
PublikationsstatusVeröffentlicht - 2 Juni 2015

Abstract

In the construction of ferrocene-based molecular wires, alkyne metathesis was investigated as an alternative to palladium-catalyzed coupling reactions for the synthesis of alkynyl ferrocenes. With a Mortreux catalyst system [Mo(CO)6, 4-chloro- or 2-fluorophenol], (1-propynyl)ferrocenes gave the expected homo metathesis products in moderate yields. Because the Mortreux catalyst system is not compatible with 1,1′-dialkynylferrocenes, a nitridomolybdenum catalyst introduced by Fürstner was tested in bidirectional homo and cross-alkyne metathesis reactions. Although the homo alkyne metathesis products were obtained in poor yields, the cross-alkyne metathesis reactions afforded the expected products in good overall yields.

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1,1′-Dialkynylferrocenes as Substrates for Bidirectional Alkyne Metathesis Reaction. / Ma, Jingxiang; Krauße, Nico; Butenschön, Holger.
in: European Journal of Organic Chemistry, Jahrgang 2015, Nr. 20, 02.06.2015, S. 4510-4518.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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T1 - 1,1′-Dialkynylferrocenes as Substrates for Bidirectional Alkyne Metathesis Reaction

AU - Ma, Jingxiang

AU - Krauße, Nico

AU - Butenschön, Holger

PY - 2015/6/2

Y1 - 2015/6/2

N2 - In the construction of ferrocene-based molecular wires, alkyne metathesis was investigated as an alternative to palladium-catalyzed coupling reactions for the synthesis of alkynyl ferrocenes. With a Mortreux catalyst system [Mo(CO)6, 4-chloro- or 2-fluorophenol], (1-propynyl)ferrocenes gave the expected homo metathesis products in moderate yields. Because the Mortreux catalyst system is not compatible with 1,1′-dialkynylferrocenes, a nitridomolybdenum catalyst introduced by Fürstner was tested in bidirectional homo and cross-alkyne metathesis reactions. Although the homo alkyne metathesis products were obtained in poor yields, the cross-alkyne metathesis reactions afforded the expected products in good overall yields.

AB - In the construction of ferrocene-based molecular wires, alkyne metathesis was investigated as an alternative to palladium-catalyzed coupling reactions for the synthesis of alkynyl ferrocenes. With a Mortreux catalyst system [Mo(CO)6, 4-chloro- or 2-fluorophenol], (1-propynyl)ferrocenes gave the expected homo metathesis products in moderate yields. Because the Mortreux catalyst system is not compatible with 1,1′-dialkynylferrocenes, a nitridomolybdenum catalyst introduced by Fürstner was tested in bidirectional homo and cross-alkyne metathesis reactions. Although the homo alkyne metathesis products were obtained in poor yields, the cross-alkyne metathesis reactions afforded the expected products in good overall yields.

KW - 1,1′-Dialkynylferrocenes

KW - Metathesis

KW - Molecular devices

KW - Sandwich complexes

KW - Synthetic methods

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JO - European Journal of Organic Chemistry

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