Green catalysts: Solid-phase peptide carbene ligands in aqueous transition-metal catalysis

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Standard

Green catalysts : Solid-phase peptide carbene ligands in aqueous transition-metal catalysis. / Worm-Leonhard, Kasper; Meldal, Morten.

I: European Journal of Organic Chemistry, Nr. 31, 11.2008, s. 5244-5253.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Worm-Leonhard, K & Meldal, M 2008, 'Green catalysts: Solid-phase peptide carbene ligands in aqueous transition-metal catalysis', European Journal of Organic Chemistry, nr. 31, s. 5244-5253. https://doi.org/10.1002/ejoc.200800633

APA

Worm-Leonhard, K., & Meldal, M. (2008). Green catalysts: Solid-phase peptide carbene ligands in aqueous transition-metal catalysis. European Journal of Organic Chemistry, (31), 5244-5253. https://doi.org/10.1002/ejoc.200800633

Vancouver

Worm-Leonhard K, Meldal M. Green catalysts: Solid-phase peptide carbene ligands in aqueous transition-metal catalysis. European Journal of Organic Chemistry. 2008 nov.;(31):5244-5253. https://doi.org/10.1002/ejoc.200800633

Author

Worm-Leonhard, Kasper ; Meldal, Morten. / Green catalysts : Solid-phase peptide carbene ligands in aqueous transition-metal catalysis. I: European Journal of Organic Chemistry. 2008 ; Nr. 31. s. 5244-5253.

Bibtex

@article{6dace444878f4c53a31996a46af65527,
title = "Green catalysts: Solid-phase peptide carbene ligands in aqueous transition-metal catalysis",
abstract = "A series of functionalized imidazolium ions containing a pyridine moiety and carboxylic acid functionality has been synthesized in solution. These compounds serve as N-heterocyclic carbene precursors and were attached to a dipeptide on solid support by means of standard peptide coupling techniques. Treatment with base generated the corresponding carbenes, which were directly complexed to palladium(II) and subsequently studied by mass spectrometry and NMR spectroscopy. The supported monocarbene catalyst 7 was successfully applied in Sonogashira and Suzuki cross-coupling reactions, and the cross-coupling products were isolated in excellent yield. Bis(carbene) catalyst 8 was successfully applied in solution in high-yielding Suzuki cross-coupling reactions. Furthermore, the catalysts proved to be stable in aqueous media, which allowed the Suzuki cross-coupling reactions to be performed in water. No loss of catalytic activity was observed when supported catalyst 7 was recycled and subjected to repetitive cycles of Suzuki cross-coupling reactions in water.",
keywords = "N-Heterocyclic carbenes, Palladium catalysts, Pyridine ligands, Solid-phase synthesis",
author = "Kasper Worm-Leonhard and Morten Meldal",
year = "2008",
month = nov,
doi = "10.1002/ejoc.200800633",
language = "English",
pages = "5244--5253",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "31",

}

RIS

TY - JOUR

T1 - Green catalysts

T2 - Solid-phase peptide carbene ligands in aqueous transition-metal catalysis

AU - Worm-Leonhard, Kasper

AU - Meldal, Morten

PY - 2008/11

Y1 - 2008/11

N2 - A series of functionalized imidazolium ions containing a pyridine moiety and carboxylic acid functionality has been synthesized in solution. These compounds serve as N-heterocyclic carbene precursors and were attached to a dipeptide on solid support by means of standard peptide coupling techniques. Treatment with base generated the corresponding carbenes, which were directly complexed to palladium(II) and subsequently studied by mass spectrometry and NMR spectroscopy. The supported monocarbene catalyst 7 was successfully applied in Sonogashira and Suzuki cross-coupling reactions, and the cross-coupling products were isolated in excellent yield. Bis(carbene) catalyst 8 was successfully applied in solution in high-yielding Suzuki cross-coupling reactions. Furthermore, the catalysts proved to be stable in aqueous media, which allowed the Suzuki cross-coupling reactions to be performed in water. No loss of catalytic activity was observed when supported catalyst 7 was recycled and subjected to repetitive cycles of Suzuki cross-coupling reactions in water.

AB - A series of functionalized imidazolium ions containing a pyridine moiety and carboxylic acid functionality has been synthesized in solution. These compounds serve as N-heterocyclic carbene precursors and were attached to a dipeptide on solid support by means of standard peptide coupling techniques. Treatment with base generated the corresponding carbenes, which were directly complexed to palladium(II) and subsequently studied by mass spectrometry and NMR spectroscopy. The supported monocarbene catalyst 7 was successfully applied in Sonogashira and Suzuki cross-coupling reactions, and the cross-coupling products were isolated in excellent yield. Bis(carbene) catalyst 8 was successfully applied in solution in high-yielding Suzuki cross-coupling reactions. Furthermore, the catalysts proved to be stable in aqueous media, which allowed the Suzuki cross-coupling reactions to be performed in water. No loss of catalytic activity was observed when supported catalyst 7 was recycled and subjected to repetitive cycles of Suzuki cross-coupling reactions in water.

KW - N-Heterocyclic carbenes

KW - Palladium catalysts

KW - Pyridine ligands

KW - Solid-phase synthesis

UR - http://www.scopus.com/inward/record.url?scp=55049101760&partnerID=8YFLogxK

U2 - 10.1002/ejoc.200800633

DO - 10.1002/ejoc.200800633

M3 - Journal article

AN - SCOPUS:55049101760

SP - 5244

EP - 5253

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 31

ER -

ID: 321825543