(Ferrocenylthienyl)phosphines for the Suzuki-Miyaura C,C coupling

Christian Gaebler; Marcus Korb; Dieter Schaarschmidt; J. Marthaeus Speck; Alexander Hildebrandt; Heinrich Lang

doi:10.1016/j.inoche.2015.02.018

(Ferrocenylthienyl)phosphines for the Suzuki-Miyaura C,C coupling

Christian Gaebler, Marcus Korb, Dieter Schaarschmidt, J. Marthaeus Speck, Alexander Hildebrandt, Heinrich Lang

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

10 Citations (Scopus)

Abstract

2-(3-Ferrocenylthienyl)phosphines of type 2-PR2-3-Fc-(C4H2S)-C-c (R = Bu-t (2); R = Ph (3); Fc = Fe(eta(5)-C5H4)(eta(5)-C5H5)) were synthesized and the structures of 2 and 3 in the solid state were determined by single X-ray structure analysis. Inter- and intra-molecular T-shaped pi center dot center dot center dot pi stackings involving cyclopentadienyl and phenyl rings are characteristic for 3. The application of 2 and 3 as ligands in the Pd-catalyzed Suzuki-Miyaura C,C cross-coupling of aryl halides with boronic acids to give the respective biaryls is reported. Electron-rich, electron-poor and sterically hindered substrates could be coupled with high yields at Pd-loadings as low as 0.1 mol%. (C) 2015 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	96-99
Number of pages	4
Journal	Inorganic Chemistry Communications
Volume	54
DOIs	https://doi.org/10.1016/j.inoche.2015.02.018
Publication status	Published - Apr 2015
Externally published	Yes

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10.1016/j.inoche.2015.02.018

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@article{de4fdf6766e14de0a2b10c7c8d538592,

title = "(Ferrocenylthienyl)phosphines for the Suzuki-Miyaura C,C coupling",

abstract = "2-(3-Ferrocenylthienyl)phosphines of type 2-PR2-3-Fc-(C4H2S)-C-c (R = Bu-t (2); R = Ph (3); Fc = Fe(eta(5)-C5H4)(eta(5)-C5H5)) were synthesized and the structures of 2 and 3 in the solid state were determined by single X-ray structure analysis. Inter- and intra-molecular T-shaped pi center dot center dot center dot pi stackings involving cyclopentadienyl and phenyl rings are characteristic for 3. The application of 2 and 3 as ligands in the Pd-catalyzed Suzuki-Miyaura C,C cross-coupling of aryl halides with boronic acids to give the respective biaryls is reported. Electron-rich, electron-poor and sterically hindered substrates could be coupled with high yields at Pd-loadings as low as 0.1 mol%. (C) 2015 Elsevier B.V. All rights reserved.",

keywords = "Suzuki-Miyaura, C,C coupling, Phosphine thiophenes, Homogenous catalysis, Solid state structure, 5-MEMBERED HETEROCYCLES, FERROCENE LIGANDS, ORGANIC-SYNTHESIS, ARYL CHLORIDES, PALLADIUM, ELECTROCHEMISTRY, DERIVATIVES, PHOSPHINE, CATALYSTS, POLYCONDENSATION",

author = "Christian Gaebler and Marcus Korb and Dieter Schaarschmidt and Speck, {J. Marthaeus} and Alexander Hildebrandt and Heinrich Lang",

year = "2015",

month = apr,

doi = "10.1016/j.inoche.2015.02.018",

language = "English",

volume = "54",

pages = "96--99",

journal = "Inorganic Chemistry Communications",

issn = "1387-7003",

publisher = "Pergamon",

}

TY - JOUR

T1 - (Ferrocenylthienyl)phosphines for the Suzuki-Miyaura C,C coupling

AU - Gaebler, Christian

AU - Korb, Marcus

AU - Schaarschmidt, Dieter

AU - Speck, J. Marthaeus

AU - Hildebrandt, Alexander

AU - Lang, Heinrich

PY - 2015/4

Y1 - 2015/4

N2 - 2-(3-Ferrocenylthienyl)phosphines of type 2-PR2-3-Fc-(C4H2S)-C-c (R = Bu-t (2); R = Ph (3); Fc = Fe(eta(5)-C5H4)(eta(5)-C5H5)) were synthesized and the structures of 2 and 3 in the solid state were determined by single X-ray structure analysis. Inter- and intra-molecular T-shaped pi center dot center dot center dot pi stackings involving cyclopentadienyl and phenyl rings are characteristic for 3. The application of 2 and 3 as ligands in the Pd-catalyzed Suzuki-Miyaura C,C cross-coupling of aryl halides with boronic acids to give the respective biaryls is reported. Electron-rich, electron-poor and sterically hindered substrates could be coupled with high yields at Pd-loadings as low as 0.1 mol%. (C) 2015 Elsevier B.V. All rights reserved.

AB - 2-(3-Ferrocenylthienyl)phosphines of type 2-PR2-3-Fc-(C4H2S)-C-c (R = Bu-t (2); R = Ph (3); Fc = Fe(eta(5)-C5H4)(eta(5)-C5H5)) were synthesized and the structures of 2 and 3 in the solid state were determined by single X-ray structure analysis. Inter- and intra-molecular T-shaped pi center dot center dot center dot pi stackings involving cyclopentadienyl and phenyl rings are characteristic for 3. The application of 2 and 3 as ligands in the Pd-catalyzed Suzuki-Miyaura C,C cross-coupling of aryl halides with boronic acids to give the respective biaryls is reported. Electron-rich, electron-poor and sterically hindered substrates could be coupled with high yields at Pd-loadings as low as 0.1 mol%. (C) 2015 Elsevier B.V. All rights reserved.

KW - Suzuki-Miyaura

KW - C,C coupling

KW - Phosphine thiophenes

KW - Homogenous catalysis

KW - Solid state structure

KW - 5-MEMBERED HETEROCYCLES

KW - FERROCENE LIGANDS

KW - ORGANIC-SYNTHESIS

KW - ARYL CHLORIDES

KW - PALLADIUM

KW - ELECTROCHEMISTRY

KW - DERIVATIVES

KW - PHOSPHINE

KW - CATALYSTS

KW - POLYCONDENSATION

U2 - 10.1016/j.inoche.2015.02.018

DO - 10.1016/j.inoche.2015.02.018

M3 - Article

SN - 1387-7003

VL - 54

SP - 96

EP - 99

JO - Inorganic Chemistry Communications

JF - Inorganic Chemistry Communications

ER -

(Ferrocenylthienyl)phosphines for the Suzuki-Miyaura C,C coupling

Abstract

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