Cross-coupling of aryl halides and triflates with intramolecularly stabilized group 13-metal alkylating reagents in the presence of mixed-metal catalysts

Margarita Shenglof; Dmitri Gelman; Bernd Heymer; Herbert Schumann; Gary A. Molander; Jochanan Blum

doi:10.1055/s-2003-36833

Cross-coupling of aryl halides and triflates with intramolecularly stabilized group 13-metal alkylating reagents in the presence of mixed-metal catalysts

Margarita Shenglof, Dmitri Gelman, Bernd Heymer, Herbert Schumann, Gary A. Molander, Jochanan Blum^*

^*Corresponding author for this work

Institute of Chemistry

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

19 Scopus citations

Abstract

In the presence of tertiary phosphines, the palladium-containing mixed-metal complexes [(CO)₄Fe(μ-PPh₂)Pd(μ-Cl)]₂(1) and [(CO)₃Co]₂(μ-CO)Pd[μ-(Ph₂PCH ₂)₂] (2) catalyze the cross-coupling of aryl triflates and halides (including chlorides) with intramolecularly stabilized dialkylaluminum, -gallium and -indium reagents 3-8. The reactions are high yielding, and homocoupling and hydrodehalogenation processes are minimal even when the alkyl moieties of the alkylating reagents contain β-hydrogen atoms. As the components of the mixed-metal complexes are either poor catalysts, or completely inactive, the high catalytic activity of 1 and 2 is attributed to synergism between the different metal nuclei of the catalysts.

Original language	American English
Pages (from-to)	302-306
Number of pages	5
Journal	Synthesis
Issue number	2
DOIs	https://doi.org/10.1055/s-2003-36833
State	Published - 2003

Keywords

Aryl halides
Cross-coupling
Group 13-metal complexes
Mixed-metal catalysts

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10.1055/s-2003-36833

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@article{14944c308dd74d339796f8b856351e9b,

title = "Cross-coupling of aryl halides and triflates with intramolecularly stabilized group 13-metal alkylating reagents in the presence of mixed-metal catalysts",

abstract = "In the presence of tertiary phosphines, the palladium-containing mixed-metal complexes [(CO)4Fe(μ-PPh2)Pd(μ-Cl)]2(1) and [(CO)3Co]2(μ-CO)Pd[μ-(Ph2PCH 2)2] (2) catalyze the cross-coupling of aryl triflates and halides (including chlorides) with intramolecularly stabilized dialkylaluminum, -gallium and -indium reagents 3-8. The reactions are high yielding, and homocoupling and hydrodehalogenation processes are minimal even when the alkyl moieties of the alkylating reagents contain β-hydrogen atoms. As the components of the mixed-metal complexes are either poor catalysts, or completely inactive, the high catalytic activity of 1 and 2 is attributed to synergism between the different metal nuclei of the catalysts.",

keywords = "Aryl halides, Cross-coupling, Group 13-metal complexes, Mixed-metal catalysts",

author = "Margarita Shenglof and Dmitri Gelman and Bernd Heymer and Herbert Schumann and Molander, {Gary A.} and Jochanan Blum",

year = "2003",

doi = "10.1055/s-2003-36833",

language = "American English",

pages = "302--306",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "2",

}

TY - JOUR

T1 - Cross-coupling of aryl halides and triflates with intramolecularly stabilized group 13-metal alkylating reagents in the presence of mixed-metal catalysts

AU - Shenglof, Margarita

AU - Gelman, Dmitri

AU - Heymer, Bernd

AU - Schumann, Herbert

AU - Molander, Gary A.

AU - Blum, Jochanan

PY - 2003

Y1 - 2003

N2 - In the presence of tertiary phosphines, the palladium-containing mixed-metal complexes [(CO)4Fe(μ-PPh2)Pd(μ-Cl)]2(1) and [(CO)3Co]2(μ-CO)Pd[μ-(Ph2PCH 2)2] (2) catalyze the cross-coupling of aryl triflates and halides (including chlorides) with intramolecularly stabilized dialkylaluminum, -gallium and -indium reagents 3-8. The reactions are high yielding, and homocoupling and hydrodehalogenation processes are minimal even when the alkyl moieties of the alkylating reagents contain β-hydrogen atoms. As the components of the mixed-metal complexes are either poor catalysts, or completely inactive, the high catalytic activity of 1 and 2 is attributed to synergism between the different metal nuclei of the catalysts.

AB - In the presence of tertiary phosphines, the palladium-containing mixed-metal complexes [(CO)4Fe(μ-PPh2)Pd(μ-Cl)]2(1) and [(CO)3Co]2(μ-CO)Pd[μ-(Ph2PCH 2)2] (2) catalyze the cross-coupling of aryl triflates and halides (including chlorides) with intramolecularly stabilized dialkylaluminum, -gallium and -indium reagents 3-8. The reactions are high yielding, and homocoupling and hydrodehalogenation processes are minimal even when the alkyl moieties of the alkylating reagents contain β-hydrogen atoms. As the components of the mixed-metal complexes are either poor catalysts, or completely inactive, the high catalytic activity of 1 and 2 is attributed to synergism between the different metal nuclei of the catalysts.

KW - Aryl halides

KW - Cross-coupling

KW - Group 13-metal complexes

KW - Mixed-metal catalysts

UR - http://www.scopus.com/inward/record.url?scp=0037286755&partnerID=8YFLogxK

U2 - 10.1055/s-2003-36833

DO - 10.1055/s-2003-36833

M3 - Article

AN - SCOPUS:0037286755

SN - 0039-7881

SP - 302

EP - 306

JO - Synthesis

JF - Synthesis

IS - 2

ER -

Cross-coupling of aryl halides and triflates with intramolecularly stabilized group 13-metal alkylating reagents in the presence of mixed-metal catalysts

Abstract

Keywords

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