Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite
A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process. A simple protocol for...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-02, Vol.56 (7), p.1840-1844 |
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| container_end_page | 1844 |
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| container_issue | 7 |
| container_start_page | 1840 |
| container_title | Angewandte Chemie International Edition |
| container_volume | 56 |
| creator | Ong, Derek Yiren Tejo, Ciputra Xu, Kai Hirao, Hajime Chiba, Shunsuke |
| description | A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process.
A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies show that an unusual concerted nucleophilic aromatic substitution operates in the present process. |
| doi_str_mv | 10.1002/anie.201611495 |
| format | Article |
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A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies show that an unusual concerted nucleophilic aromatic substitution operates in the present process.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201611495</identifier><identifier>PMID: 28071853</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Aromatic compounds ; DFT calculations ; haloarenes ; hydrodehalogenation ; Iodides ; Lithium ; reduction ; Sodium ; sodium hydride</subject><ispartof>Angewandte Chemie International Edition, 2017-02, Vol.56 (7), p.1840-1844</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5445-5043d6602da6872d7112559889344abecdd85c5a879531373607a8209580825a3</citedby><cites>FETCH-LOGICAL-c5445-5043d6602da6872d7112559889344abecdd85c5a879531373607a8209580825a3</cites><orcidid>0000-0003-2039-023X</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.201611495$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201611495$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28071853$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ong, Derek Yiren</creatorcontrib><creatorcontrib>Tejo, Ciputra</creatorcontrib><creatorcontrib>Xu, Kai</creatorcontrib><creatorcontrib>Hirao, Hajime</creatorcontrib><creatorcontrib>Chiba, Shunsuke</creatorcontrib><title>Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite</title><title>Angewandte Chemie International Edition</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process.
A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies show that an unusual concerted nucleophilic aromatic substitution operates in the present process.</description><subject>Aromatic compounds</subject><subject>DFT calculations</subject><subject>haloarenes</subject><subject>hydrodehalogenation</subject><subject>Iodides</subject><subject>Lithium</subject><subject>reduction</subject><subject>Sodium</subject><subject>sodium hydride</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqF0btOwzAUBmALgWgprIwoEgtLiq-xPVZVIZUqGIDZcmMXUiVxsRuhbLwDb8iT4KqlSAww-aLv_Dr2AeAcwSGCEF_rprRDDFGGEJXsAPQRwyglnJPDuKeEpFww1AMnISyjFwJmx6CHBeRIMNIHed4Z74x90ZV7to1el65J3CLJ41l729iQzLtEJw_OlG2dbHRp7Of7xzReGJuMXb1yoVzbU3C00FWwZ7t1AJ5uJo_jPJ3d307Ho1laMEpZyiAlJssgNjoTHBuOEGZMCiEJpXpuC2MEK5gWXDKCCCcZ5FpgKJmAAjNNBuBqm7vy7rW1Ya3qMhS2qnRjXRtUfBaPZZCQSC9_0aVrfRO7U0giTClBOPtTiQzHXjmUUQ23qvAuBG8XauXLWvtOIag2k1CbSaj9JGLBxS62ndfW7Pn310cgt-CtrGz3T5wa3U0nP-Ff-CqR5w</recordid><startdate>20170206</startdate><enddate>20170206</enddate><creator>Ong, Derek Yiren</creator><creator>Tejo, Ciputra</creator><creator>Xu, Kai</creator><creator>Hirao, Hajime</creator><creator>Chiba, Shunsuke</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2039-023X</orcidid></search><sort><creationdate>20170206</creationdate><title>Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite</title><author>Ong, Derek Yiren ; Tejo, Ciputra ; Xu, Kai ; Hirao, Hajime ; Chiba, Shunsuke</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5445-5043d6602da6872d7112559889344abecdd85c5a879531373607a8209580825a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aromatic compounds</topic><topic>DFT calculations</topic><topic>haloarenes</topic><topic>hydrodehalogenation</topic><topic>Iodides</topic><topic>Lithium</topic><topic>reduction</topic><topic>Sodium</topic><topic>sodium hydride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ong, Derek Yiren</creatorcontrib><creatorcontrib>Tejo, Ciputra</creatorcontrib><creatorcontrib>Xu, Kai</creatorcontrib><creatorcontrib>Hirao, Hajime</creatorcontrib><creatorcontrib>Chiba, Shunsuke</creatorcontrib><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>Ong, Derek Yiren</au><au>Tejo, Ciputra</au><au>Xu, Kai</au><au>Hirao, Hajime</au><au>Chiba, Shunsuke</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-02-06</date><risdate>2017</risdate><volume>56</volume><issue>7</issue><spage>1840</spage><epage>1844</epage><pages>1840-1844</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A simple protocol for hydrodebromination and ‐deiodination of halo(hetero)arenes was enabled by sodium hydride (NaH) in the presence of lithium iodide (LiI). Mechanistic studies showed that an unusual concerted nucleophilic aromatic substitution operates in the present process.
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aromatic compounds DFT calculations haloarenes hydrodehalogenation Iodides Lithium reduction Sodium sodium hydride |
| title | Hydrodehalogenation of Haloarenes by a Sodium Hydride–Iodide Composite |
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