Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

Mansur B. Ibrahim; Bassam El Ali; Imran Malik; Mohammed Fettouhi

doi:10.1016/j.tetlet.2015.12.086

Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

Mansur B. Ibrahim, Bassam El Ali^*, Imran Malik, Mohammed Fettouhi

^*Corresponding author for this work

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

12 Scopus citations

Abstract

A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH₃CN-H₂O solvent system allowed for the cross-coupling reactions to proceed at room temperature or 60 °C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross-coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes.

Original language	English
Pages (from-to)	554-558
Number of pages	5
Journal	Tetrahedron Letters
Volume	57
Issue number	5
DOIs	https://doi.org/10.1016/j.tetlet.2015.12.086
State	Published - 3 Feb 2016

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Ltd. All rights reserved.

Keywords

Alkyl alkynes
Dialkynes
Diiodobenzene
Palladium-bis(oxazoline)
Sonogashira coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.12.086

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title = "Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions",

abstract = "A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol \% of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross-coupling reactions to proceed at room temperature or 60 °C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross-coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes.",

keywords = "Alkyl alkynes, Dialkynes, Diiodobenzene, Palladium-bis(oxazoline), Sonogashira coupling",

author = "Ibrahim, \{Mansur B.\} and Ali, \{Bassam El\} and Imran Malik and Mohammed Fettouhi",

year = "2016",

month = feb,

day = "3",

doi = "10.1016/j.tetlet.2015.12.086",

language = "English",

volume = "57",

pages = "554--558",

journal = "Tetrahedron Letters",

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number = "5",

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TY - JOUR

T1 - Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

AU - Ibrahim, Mansur B.

AU - Ali, Bassam El

AU - Malik, Imran

AU - Fettouhi, Mohammed

PY - 2016/2/3

Y1 - 2016/2/3

N2 - A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross-coupling reactions to proceed at room temperature or 60 °C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross-coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes.

AB - A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross-coupling reactions to proceed at room temperature or 60 °C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross-coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes.

KW - Alkyl alkynes

KW - Dialkynes

KW - Diiodobenzene

KW - Palladium-bis(oxazoline)

KW - Sonogashira coupling

UR - https://www.scopus.com/pages/publications/84954387280

U2 - 10.1016/j.tetlet.2015.12.086

DO - 10.1016/j.tetlet.2015.12.086

M3 - Article

AN - SCOPUS:84954387280

SN - 0040-4039

VL - 57

SP - 554

EP - 558

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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