Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO

Andrei S. Batsanov; Javier A. Cabeza; Marco G. Crestani; Manuel R. Fructos; Pablo García-Álvarez; Marie Gille; Zhenyang Lin; Todd B. Marder

doi:10.1002/anie.201601121

Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO

Andrei S. Batsanov, Javier A. Cabeza^*, Marco G. Crestani, Manuel R. Fructos, Pablo García-Álvarez, Marie Gille, Zhenyang Lin, Todd B. Marder

^*Corresponding author for this work

Department of Chemistry

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

26 Citations (Scopus)

Abstract

Many transition-metal complexes and some metal-free compounds are able to bind carbon monoxide, a molecule which has the strongest chemical bond in nature. However, very few of them have been shown to induce the cleavage of its C-O bond and even fewer are those that are able to transform CO into organic reagents with potential in organic synthesis. This work shows that bis(pinacolato)diboron, B₂pin₂, reacts with ruthenium carbonyl to give metallic complexes containing borylmethylidyne (CBpin) and diborylethyne (pinBC≡CBpin) ligands and also metal-free perborylated C₁ and C₂ products, such as C(Bpin)₄ and C₂(Bpin)₆, respectively, which have great potential as building blocks for Suzuki-Miyaura cross-coupling and other reactions. The use of ¹³CO-enriched ruthenium carbonyl has demonstrated that the boron-bound carbon atoms of all of these reaction products arise from CO ligands.

Original language	English
Pages (from-to)	4707-4710
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	15
DOIs	https://doi.org/10.1002/anie.201601121
Publication status	Published - 4 Apr 2016

Bibliographical note

Publisher Copyright:
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords

boron
borylation
carbon monoxide
cluster compounds
ruthenium

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10.1002/anie.201601121

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title = "Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO",

abstract = "Many transition-metal complexes and some metal-free compounds are able to bind carbon monoxide, a molecule which has the strongest chemical bond in nature. However, very few of them have been shown to induce the cleavage of its C-O bond and even fewer are those that are able to transform CO into organic reagents with potential in organic synthesis. This work shows that bis(pinacolato)diboron, B2pin2, reacts with ruthenium carbonyl to give metallic complexes containing borylmethylidyne (CBpin) and diborylethyne (pinBC≡CBpin) ligands and also metal-free perborylated C1 and C2 products, such as C(Bpin)4 and C2(Bpin)6, respectively, which have great potential as building blocks for Suzuki-Miyaura cross-coupling and other reactions. The use of 13CO-enriched ruthenium carbonyl has demonstrated that the boron-bound carbon atoms of all of these reaction products arise from CO ligands.",

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note = "Publisher Copyright: {\textcopyright} 2016 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim.",

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T1 - Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO

AU - Batsanov, Andrei S.

AU - Cabeza, Javier A.

AU - Crestani, Marco G.

AU - Fructos, Manuel R.

AU - García-Álvarez, Pablo

AU - Gille, Marie

AU - Lin, Zhenyang

AU - Marder, Todd B.

PY - 2016/4/4

Y1 - 2016/4/4

N2 - Many transition-metal complexes and some metal-free compounds are able to bind carbon monoxide, a molecule which has the strongest chemical bond in nature. However, very few of them have been shown to induce the cleavage of its C-O bond and even fewer are those that are able to transform CO into organic reagents with potential in organic synthesis. This work shows that bis(pinacolato)diboron, B2pin2, reacts with ruthenium carbonyl to give metallic complexes containing borylmethylidyne (CBpin) and diborylethyne (pinBC≡CBpin) ligands and also metal-free perborylated C1 and C2 products, such as C(Bpin)4 and C2(Bpin)6, respectively, which have great potential as building blocks for Suzuki-Miyaura cross-coupling and other reactions. The use of 13CO-enriched ruthenium carbonyl has demonstrated that the boron-bound carbon atoms of all of these reaction products arise from CO ligands.

AB - Many transition-metal complexes and some metal-free compounds are able to bind carbon monoxide, a molecule which has the strongest chemical bond in nature. However, very few of them have been shown to induce the cleavage of its C-O bond and even fewer are those that are able to transform CO into organic reagents with potential in organic synthesis. This work shows that bis(pinacolato)diboron, B2pin2, reacts with ruthenium carbonyl to give metallic complexes containing borylmethylidyne (CBpin) and diborylethyne (pinBC≡CBpin) ligands and also metal-free perborylated C1 and C2 products, such as C(Bpin)4 and C2(Bpin)6, respectively, which have great potential as building blocks for Suzuki-Miyaura cross-coupling and other reactions. The use of 13CO-enriched ruthenium carbonyl has demonstrated that the boron-bound carbon atoms of all of these reaction products arise from CO ligands.

KW - boron

KW - borylation

KW - carbon monoxide

KW - cluster compounds

KW - ruthenium

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UR - https://openalex.org/W2295849449

UR - https://www.scopus.com/pages/publications/84960154701

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DO - 10.1002/anie.201601121

M3 - Journal Article

SN - 1433-7851

VL - 55

SP - 4707

EP - 4710

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO

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Keywords

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