Catalytic Borylation of SCF3-Functionalized Arenes by Rhodium(I) Boryl Complexes: Regioselective CH Activation at the ortho-Position
An unprecedented reaction pathway for the borylation of SCF3‐containing arenes using [Rh(Bpin)(PEt3)3] (pin=pinacolato) is reported. Catalytic processes were developed and the functionalizations proceed under mild reaction conditions. The CH activations occur with a unique regioselectivity for the...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2014-08, Vol.53 (35), p.9311-9315 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Kalläne, Sabrina I. Braun, Thomas |
| description | An unprecedented reaction pathway for the borylation of SCF3‐containing arenes using [Rh(Bpin)(PEt3)3] (pin=pinacolato) is reported. Catalytic processes were developed and the functionalizations proceed under mild reaction conditions. The CH activations occur with a unique regioselectivity for the position ortho to the SCF3 group, which apparently serves as directing group. Borylated SCF3 compounds can serve as versatile building blocks.
SCF3 building blocks: A unique reaction route allows access to SCF3‐functionalized arenes, which are borylated at the ortho‐position. The functionalization proceeds by CH borylation with [Rh(Bpin)(PEt3)3] (pin=pinacolato), and the SCF3 group likely serves as directing group. The generated borylated SCF3 compounds are versatile building blocks for further transformations. |
| doi_str_mv | 10.1002/anie.201406424 |
| format | Article |
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SCF3 building blocks: A unique reaction route allows access to SCF3‐functionalized arenes, which are borylated at the ortho‐position. The functionalization proceeds by CH borylation with [Rh(Bpin)(PEt3)3] (pin=pinacolato), and the SCF3 group likely serves as directing group. The generated borylated SCF3 compounds are versatile building blocks for further transformations.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201406424</identifier><identifier>PMID: 25088814</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>boron ; Boron Compounds - chemical synthesis ; Boron Compounds - chemistry ; Calixarenes - chemistry ; Catalysis ; Chlorofluorocarbons, Methane - chemistry ; CH activation ; Models, Molecular ; Molecular Structure ; Organometallic Compounds - chemistry ; rhodium ; Rhodium - chemistry ; Stereoisomerism ; sulfur ; synthetic methods</subject><ispartof>Angewandte Chemie International Edition, 2014-08, Vol.53 (35), p.9311-9315</ispartof><rights>2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></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.201406424$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201406424$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25088814$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kalläne, Sabrina I.</creatorcontrib><creatorcontrib>Braun, Thomas</creatorcontrib><title>Catalytic Borylation of SCF3-Functionalized Arenes by Rhodium(I) Boryl Complexes: Regioselective CH Activation at the ortho-Position</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>An unprecedented reaction pathway for the borylation of SCF3‐containing arenes using [Rh(Bpin)(PEt3)3] (pin=pinacolato) is reported. Catalytic processes were developed and the functionalizations proceed under mild reaction conditions. The CH activations occur with a unique regioselectivity for the position ortho to the SCF3 group, which apparently serves as directing group. Borylated SCF3 compounds can serve as versatile building blocks.
SCF3 building blocks: A unique reaction route allows access to SCF3‐functionalized arenes, which are borylated at the ortho‐position. The functionalization proceeds by CH borylation with [Rh(Bpin)(PEt3)3] (pin=pinacolato), and the SCF3 group likely serves as directing group. The generated borylated SCF3 compounds are versatile building blocks for further transformations.</description><subject>boron</subject><subject>Boron Compounds - chemical synthesis</subject><subject>Boron Compounds - chemistry</subject><subject>Calixarenes - chemistry</subject><subject>Catalysis</subject><subject>Chlorofluorocarbons, Methane - chemistry</subject><subject>CH activation</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemistry</subject><subject>rhodium</subject><subject>Rhodium - chemistry</subject><subject>Stereoisomerism</subject><subject>sulfur</subject><subject>synthetic methods</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kc9u1DAQhyNERUvhyhH5WA5p7fhvuG2jbnelVYtKERIXy0kmXYMTL3FCm74AD8KD8Ei8QhOl7Mmeme-bw_yi6B3BpwTj5Mw0Fk4TTBgWLGEvoiPCExJTKenL8c8ojaXi5DB6HcL3kVcKi1fRYcKxUoqwo-h3Zjrjhs4W6Ny3gzOd9Q3yFfqcLWm87JtiahhnH6FEixYaCCgf0M3Wl7avT9YfZg1lvt45eIDwEd3AnfUBHIzqL0DZvz9_V2gxFfNy06FuC8i33dbHn3ywU_dNdFAZF-Dt83scfVle3GareHN9uc4Wm_iOyYTFphIpCEXLqshlwdOykBVNcWEIU6WgVcry6QDKGAW5MIWRUPJS5lAJkElp6HF0Mu_dtf5nD6HTtQ0FOGca8H3QhHMuEpZgPqLvn9E-r6HUu9bWph30_-ONQDoD99bBsJ8TrKdo9BSN3kejF1fri301uvHs2tDBw9417Q8tJJVcf7261PTb-YopvNG39Am4CJSs</recordid><startdate>20140825</startdate><enddate>20140825</enddate><creator>Kalläne, Sabrina I.</creator><creator>Braun, Thomas</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20140825</creationdate><title>Catalytic Borylation of SCF3-Functionalized Arenes by Rhodium(I) Boryl Complexes: Regioselective CH Activation at the ortho-Position</title><author>Kalläne, Sabrina I. ; Braun, Thomas</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g4724-af69e683dfcb7c59dc7f390ca148d63f94b15218aa8eb6aca7ed5d7bef6e72da3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>boron</topic><topic>Boron Compounds - chemical synthesis</topic><topic>Boron Compounds - chemistry</topic><topic>Calixarenes - chemistry</topic><topic>Catalysis</topic><topic>Chlorofluorocarbons, Methane - chemistry</topic><topic>CH activation</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemistry</topic><topic>rhodium</topic><topic>Rhodium - chemistry</topic><topic>Stereoisomerism</topic><topic>sulfur</topic><topic>synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kalläne, Sabrina I.</creatorcontrib><creatorcontrib>Braun, Thomas</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kalläne, Sabrina I.</au><au>Braun, Thomas</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Borylation of SCF3-Functionalized Arenes by Rhodium(I) Boryl Complexes: Regioselective CH Activation at the ortho-Position</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2014-08-25</date><risdate>2014</risdate><volume>53</volume><issue>35</issue><spage>9311</spage><epage>9315</epage><pages>9311-9315</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>An unprecedented reaction pathway for the borylation of SCF3‐containing arenes using [Rh(Bpin)(PEt3)3] (pin=pinacolato) is reported. Catalytic processes were developed and the functionalizations proceed under mild reaction conditions. The CH activations occur with a unique regioselectivity for the position ortho to the SCF3 group, which apparently serves as directing group. Borylated SCF3 compounds can serve as versatile building blocks.
SCF3 building blocks: A unique reaction route allows access to SCF3‐functionalized arenes, which are borylated at the ortho‐position. The functionalization proceeds by CH borylation with [Rh(Bpin)(PEt3)3] (pin=pinacolato), and the SCF3 group likely serves as directing group. The generated borylated SCF3 compounds are versatile building blocks for further transformations.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25088814</pmid><doi>10.1002/anie.201406424</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1433-7851 |
| ispartof | Angewandte Chemie International Edition, 2014-08, Vol.53 (35), p.9311-9315 |
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| language | eng |
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| source | Wiley Online Library - AutoHoldings Journals; MEDLINE |
| subjects | boron Boron Compounds - chemical synthesis Boron Compounds - chemistry Calixarenes - chemistry Catalysis Chlorofluorocarbons, Methane - chemistry CH activation Models, Molecular Molecular Structure Organometallic Compounds - chemistry rhodium Rhodium - chemistry Stereoisomerism sulfur synthetic methods |
| title | Catalytic Borylation of SCF3-Functionalized Arenes by Rhodium(I) Boryl Complexes: Regioselective CH Activation at the ortho-Position |
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