Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO
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 org...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-04, Vol.55 (15), p.4707-4710 |
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| creator | Batsanov, Andrei S. Cabeza, Javier A. Crestani, Marco G. Fructos, Manuel R. García-Álvarez, Pablo Gille, Marie Lin, Zhenyang Marder, Todd B. |
| description | 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.
Piñacolato: The C−O bond of coordinated carbon monoxide can be cleaved by a diborane(4) compound. A combination of bis(pinacolato)diboron, B2pin2, with ruthenium carbonyl promotes the cleavage and reductive coupling of coordinated CO to give not only metallic complexes containing either CBpin or C2(Bpin)2 ligands but also metal‐free highly borylated organic molecules, such as C(Bpin)4 and C2(Bpin)6. |
| doi_str_mv | 10.1002/anie.201601121 |
| format | Article |
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Piñacolato: The C−O bond of coordinated carbon monoxide can be cleaved by a diborane(4) compound. A combination of bis(pinacolato)diboron, B2pin2, with ruthenium carbonyl promotes the cleavage and reductive coupling of coordinated CO to give not only metallic complexes containing either CBpin or C2(Bpin)2 ligands but also metal‐free highly borylated organic molecules, such as C(Bpin)4 and C2(Bpin)6.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201601121</identifier><identifier>PMID: 26953905</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Boron ; borylation ; Carbon monoxide ; Carbonyls ; Chemical bonds ; Chemical reactions ; Cleavage ; cluster compounds ; Coordination compounds ; Cross coupling ; Ductile-brittle transition ; Enrichment ; Ethane ; Fracture mechanics ; Ligands ; Metal complexes ; Metals ; Methane ; Reaction products ; Reagents ; Ruthenium</subject><ispartof>Angewandte Chemie International Edition, 2016-04, Vol.55 (15), p.4707-4710</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5421-99dd9552d743fee0b8cec79b7174c8e8e083f5d7d2559b33994311b7592f82ab3</citedby><cites>FETCH-LOGICAL-c5421-99dd9552d743fee0b8cec79b7174c8e8e083f5d7d2559b33994311b7592f82ab3</cites><orcidid>0000-0001-8563-9193</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201601121$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201601121$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26953905$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Batsanov, Andrei S.</creatorcontrib><creatorcontrib>Cabeza, Javier A.</creatorcontrib><creatorcontrib>Crestani, Marco G.</creatorcontrib><creatorcontrib>Fructos, Manuel R.</creatorcontrib><creatorcontrib>García-Álvarez, Pablo</creatorcontrib><creatorcontrib>Gille, Marie</creatorcontrib><creatorcontrib>Lin, Zhenyang</creatorcontrib><creatorcontrib>Marder, Todd B.</creatorcontrib><title>Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>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.
Piñacolato: The C−O bond of coordinated carbon monoxide can be cleaved by a diborane(4) compound. A combination of bis(pinacolato)diboron, B2pin2, with ruthenium carbonyl promotes the cleavage and reductive coupling of coordinated CO to give not only metallic complexes containing either CBpin or C2(Bpin)2 ligands but also metal‐free highly borylated organic molecules, such as C(Bpin)4 and C2(Bpin)6.</description><subject>Boron</subject><subject>borylation</subject><subject>Carbon monoxide</subject><subject>Carbonyls</subject><subject>Chemical bonds</subject><subject>Chemical reactions</subject><subject>Cleavage</subject><subject>cluster compounds</subject><subject>Coordination compounds</subject><subject>Cross coupling</subject><subject>Ductile-brittle transition</subject><subject>Enrichment</subject><subject>Ethane</subject><subject>Fracture mechanics</subject><subject>Ligands</subject><subject>Metal complexes</subject><subject>Metals</subject><subject>Methane</subject><subject>Reaction products</subject><subject>Reagents</subject><subject>Ruthenium</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkc1v1DAQxS0EoqXlyhFF4sIli8eOY_tYot226pf6gThaTjxpU7zJNk6g-e9xSVkhDjCXmcPvPT3NI-Qd0AVQyj7ZtsEFo5BTAAYvyC4IBimXkr-Md8Z5KpWAHfImhPvIK0Xz12SH5VpwTcUuuVmN3k_J566fvB3QJWc43NkWE9u6ZDmf5ZRcjcMdts24Ts_QNb_AwqP9bm9nsujGjW_a26Srk-Jin7yqrQ_49nnvkS-r5U1xlJ5eHB4XB6dpJbKYUmvntBDMyYzXiLRUFVZSlxJkVilUSBWvhZOOCaFLzrXOOEAphWa1Yrbke-Tj7Lvpu4cRw2DWTajQ-5i6G4MBKVVGqZYQ0Q9_offd2LcxnQFN85zSPD7rX5SMkwMIFanFTFV9F0KPtdn0zdr2kwFqnloxT62YbStR8P7ZdizX6Lb47xoioGfgR-Nx-o-dOTg_Xv5pns7aJgz4uNXa_pvJJZfCfD0_NNcnK3XJsxNT8J9o9aSx</recordid><startdate>20160404</startdate><enddate>20160404</enddate><creator>Batsanov, Andrei S.</creator><creator>Cabeza, Javier A.</creator><creator>Crestani, Marco G.</creator><creator>Fructos, Manuel R.</creator><creator>García-Álvarez, Pablo</creator><creator>Gille, Marie</creator><creator>Lin, Zhenyang</creator><creator>Marder, Todd B.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8563-9193</orcidid></search><sort><creationdate>20160404</creationdate><title>Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO</title><author>Batsanov, Andrei S. ; Cabeza, Javier A. ; Crestani, Marco G. ; Fructos, Manuel R. ; García-Álvarez, Pablo ; Gille, Marie ; Lin, Zhenyang ; Marder, Todd B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5421-99dd9552d743fee0b8cec79b7174c8e8e083f5d7d2559b33994311b7592f82ab3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Boron</topic><topic>borylation</topic><topic>Carbon monoxide</topic><topic>Carbonyls</topic><topic>Chemical bonds</topic><topic>Chemical reactions</topic><topic>Cleavage</topic><topic>cluster compounds</topic><topic>Coordination compounds</topic><topic>Cross coupling</topic><topic>Ductile-brittle transition</topic><topic>Enrichment</topic><topic>Ethane</topic><topic>Fracture mechanics</topic><topic>Ligands</topic><topic>Metal complexes</topic><topic>Metals</topic><topic>Methane</topic><topic>Reaction products</topic><topic>Reagents</topic><topic>Ruthenium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Batsanov, Andrei S.</creatorcontrib><creatorcontrib>Cabeza, Javier A.</creatorcontrib><creatorcontrib>Crestani, Marco G.</creatorcontrib><creatorcontrib>Fructos, Manuel R.</creatorcontrib><creatorcontrib>García-Álvarez, Pablo</creatorcontrib><creatorcontrib>Gille, Marie</creatorcontrib><creatorcontrib>Lin, Zhenyang</creatorcontrib><creatorcontrib>Marder, Todd B.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Batsanov, Andrei S.</au><au>Cabeza, Javier A.</au><au>Crestani, Marco G.</au><au>Fructos, Manuel R.</au><au>García-Álvarez, Pablo</au><au>Gille, Marie</au><au>Lin, Zhenyang</au><au>Marder, Todd B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-04-04</date><risdate>2016</risdate><volume>55</volume><issue>15</issue><spage>4707</spage><epage>4710</epage><pages>4707-4710</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><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.
Piñacolato: The C−O bond of coordinated carbon monoxide can be cleaved by a diborane(4) compound. A combination of bis(pinacolato)diboron, B2pin2, with ruthenium carbonyl promotes the cleavage and reductive coupling of coordinated CO to give not only metallic complexes containing either CBpin or C2(Bpin)2 ligands but also metal‐free highly borylated organic molecules, such as C(Bpin)4 and C2(Bpin)6.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>26953905</pmid><doi>10.1002/anie.201601121</doi><tpages>4</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0001-8563-9193</orcidid></addata></record> |
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| subjects | Boron borylation Carbon monoxide Carbonyls Chemical bonds Chemical reactions Cleavage cluster compounds Coordination compounds Cross coupling Ductile-brittle transition Enrichment Ethane Fracture mechanics Ligands Metal complexes Metals Methane Reaction products Reagents Ruthenium |
| title | Fully Borylated Methane and Ethane by Ruthenium-Mediated Cleavage and Coupling of CO |
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