Ruphus-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates

A. van den Hoogenband; J.H.M. Lange; J.W. Terpstra; M. Koch; G.M. Visser; M. de Visser; T.J. Korstanje; J.T.B.H. Jastrzebski

doi:10.1016/j.tetlet.2008.04.129

Ruphus-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates

A. van den Hoogenband, J.H.M. Lange, J.W. Terpstra, M. Koch, G.M. Visser, M. de Visser, T.J. Korstanje, J.T.B.H. Jastrzebski

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

59 Citations (Scopus)

Abstract

A Ruphos-mediated Suzuki cross-coupling between (hetero)aryl bromides and secondary alkyltrifluoroborates is described using palladium catalysis. The Ruphos ligand showed superior properties as compared to S-Phos in this type of reaction. This method constitutes a valuable extension to current methods for the straightforward production of secondary-alkylated (hetero)aryl derivatives.

Original language	English
Pages (from-to)	4122-4124
Journal	Tetrahedron Letters
Volume	49
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.129
Publication status	Published - 2008

Keywords

palladium-catalyzed reactions
aryl halides
cyclopropylboronic acids
arylboronic acids
miyaura reaction
potassium aryl
organic-synthesis
active catalyst
boronic acids
efficient

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10.1016/j.tetlet.2008.04.129

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title = "Ruphus-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates",

abstract = "A Ruphos-mediated Suzuki cross-coupling between (hetero)aryl bromides and secondary alkyltrifluoroborates is described using palladium catalysis. The Ruphos ligand showed superior properties as compared to S-Phos in this type of reaction. This method constitutes a valuable extension to current methods for the straightforward production of secondary-alkylated (hetero)aryl derivatives.",

keywords = "palladium-catalyzed reactions, aryl halides, cyclopropylboronic acids, arylboronic acids, miyaura reaction, potassium aryl, organic-synthesis, active catalyst, boronic acids, efficient",

author = "{van den Hoogenband}, A. and J.H.M. Lange and J.W. Terpstra and M. Koch and G.M. Visser and {de Visser}, M. and T.J. Korstanje and J.T.B.H. Jastrzebski",

year = "2008",

doi = "10.1016/j.tetlet.2008.04.129",

language = "English",

volume = "49",

pages = "4122--4124",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

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TY - JOUR

T1 - Ruphus-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates

AU - van den Hoogenband, A.

AU - Lange, J.H.M.

AU - Terpstra, J.W.

AU - Koch, M.

AU - Visser, G.M.

AU - de Visser, M.

AU - Korstanje, T.J.

AU - Jastrzebski, J.T.B.H.

PY - 2008

Y1 - 2008

N2 - A Ruphos-mediated Suzuki cross-coupling between (hetero)aryl bromides and secondary alkyltrifluoroborates is described using palladium catalysis. The Ruphos ligand showed superior properties as compared to S-Phos in this type of reaction. This method constitutes a valuable extension to current methods for the straightforward production of secondary-alkylated (hetero)aryl derivatives.

AB - A Ruphos-mediated Suzuki cross-coupling between (hetero)aryl bromides and secondary alkyltrifluoroborates is described using palladium catalysis. The Ruphos ligand showed superior properties as compared to S-Phos in this type of reaction. This method constitutes a valuable extension to current methods for the straightforward production of secondary-alkylated (hetero)aryl derivatives.

KW - palladium-catalyzed reactions

KW - aryl halides

KW - cyclopropylboronic acids

KW - arylboronic acids

KW - miyaura reaction

KW - potassium aryl

KW - organic-synthesis

KW - active catalyst

KW - boronic acids

KW - efficient

U2 - 10.1016/j.tetlet.2008.04.129

DO - 10.1016/j.tetlet.2008.04.129

M3 - Article

SN - 0040-4039

VL - 49

SP - 4122

EP - 4124

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Ruphus-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates

Abstract

Keywords

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