Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds

Sergei F. Vasilevsky, Olga L. Krivenko, Igor V. Alabugin

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the formation of 4-[2-(aryl/hetarylethynyl)phenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyls in 70-75% yields.

Original languageEnglish
Pages (from-to)8246-8249
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number46
DOIs
Publication statusPublished - 12 Nov 2007
Externally publishedYes

Fingerprint

Oxidative Coupling
Imidazolines
Alkynes
Oxides
Dimerization
Catalysts
nitroxyl

Keywords

  • 3-Imidazoline-nitroxyles
  • Aryl- and hetarylacetylenes
  • Cross-coupling
  • Oxidative coupling
  • Stable radicals

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

@article{1855d32fe9f343bb80d0438642c57480,
title = "Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds",
abstract = "In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the formation of 4-[2-(aryl/hetarylethynyl)phenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyls in 70-75{\%} yields.",
keywords = "3-Imidazoline-nitroxyles, Aryl- and hetarylacetylenes, Cross-coupling, Oxidative coupling, Stable radicals",
author = "Vasilevsky, {Sergei F.} and Krivenko, {Olga L.} and Alabugin, {Igor V.}",
year = "2007",
month = "11",
day = "12",
doi = "10.1016/j.tetlet.2007.09.031",
language = "English",
volume = "48",
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journal = "Tetrahedron Letters",
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publisher = "Elsevier Limited",
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TY - JOUR

T1 - Oxidative coupling of alkynes mediated by nitroxyl radicals under Sonogashira conditions and Pd-free catalytic approach to stable radicals of 3-imidazoline family with triple bonds

AU - Vasilevsky, Sergei F.

AU - Krivenko, Olga L.

AU - Alabugin, Igor V.

PY - 2007/11/12

Y1 - 2007/11/12

N2 - In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the formation of 4-[2-(aryl/hetarylethynyl)phenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyls in 70-75% yields.

AB - In the presence of Pd catalyst, 3-imidazoline nitroxyl radicals promote oxidative coupling (dimerization) of terminal alkynes even in the absence of Cu(II) additives. On the other hand, the Pd-free CuI-PPh3-K2CO3-DMF catalytic system leads to the efficient cross-coupling of 1-hydroxy-4-[2-(p-iodophenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide with terminal aryl- and hetarylacetylenes with the formation of 4-[2-(aryl/hetarylethynyl)phenyl)vinyl]-2,2,5,5-tetramethyl-3-imidazoline-3-oxide-1-oxyls in 70-75% yields.

KW - 3-Imidazoline-nitroxyles

KW - Aryl- and hetarylacetylenes

KW - Cross-coupling

KW - Oxidative coupling

KW - Stable radicals

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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