Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes
The metal‐free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly‐polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2017-10, Vol.359 (20), p.3503-3508 |
|---|---|
| Hauptverfasser: | , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3508 |
|---|---|
| container_issue | 20 |
| container_start_page | 3503 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 359 |
| creator | Dohi, Toshifumi Koseki, Daichi Sumida, Kohei Okada, Kana Mizuno, Serina Kato, Asami Morimoto, Koji Kita, Yasuyuki |
| description | The metal‐free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly‐polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings. |
| doi_str_mv | 10.1002/adsc.201700843 |
| format | Article |
| fullrecord | <record><control><sourceid>wiley_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1002_adsc_201700843</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>ADSC201700843</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3923-e36ab30f9a59d4b0dadfc4cddb9f74d1e9eced28524c666d94221b410453cb2a3</originalsourceid><addsrcrecordid>eNqFkDFPwzAUhC0EEqWwMnuEIcV2nKQeo5SWSEUdgDly7BfJKImRnQKd6MLOb-wvwRWojEx30rvvpHcIXVIyoYSwG6m9mjBCM0KmPD5CI5rSJOI0FccHn5BTdOb9MwmxaZaN0Mc9DLLdbb_mDgCvgsndppWDsT22DS6kq-37pjUK58poXG-CDuYV8MzIEDRW296su6uyLK9x2Q_gOtBGDuDxAnpwwWls-t3205thjRtnO1wGyFvpwt2fo5NGth4ufnWMnua3j8VdtFwtyiJfRioWLI4gTmUdk0bIRGheEy11o7jSuhZNxjUFAQo0myaMqzRNteCM0ZpTwpNY1UzGYzT56VXOeu-gqV6c6cILFSXVfr5qP191mC8A4gd4My1s_klX-eyh-GO_ARmgeY8</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes</title><source>Access via Wiley Online Library</source><creator>Dohi, Toshifumi ; Koseki, Daichi ; Sumida, Kohei ; Okada, Kana ; Mizuno, Serina ; Kato, Asami ; Morimoto, Koji ; Kita, Yasuyuki</creator><creatorcontrib>Dohi, Toshifumi ; Koseki, Daichi ; Sumida, Kohei ; Okada, Kana ; Mizuno, Serina ; Kato, Asami ; Morimoto, Koji ; Kita, Yasuyuki</creatorcontrib><description>The metal‐free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly‐polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201700843</identifier><language>eng</language><subject>Arylation ; Carboxylic acids ; Hypervalent compounds ; Iodine ; Reactive intermediates</subject><ispartof>Advanced synthesis & catalysis, 2017-10, Vol.359 (20), p.3503-3508</ispartof><rights>2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3923-e36ab30f9a59d4b0dadfc4cddb9f74d1e9eced28524c666d94221b410453cb2a3</citedby><cites>FETCH-LOGICAL-c3923-e36ab30f9a59d4b0dadfc4cddb9f74d1e9eced28524c666d94221b410453cb2a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.201700843$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201700843$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Dohi, Toshifumi</creatorcontrib><creatorcontrib>Koseki, Daichi</creatorcontrib><creatorcontrib>Sumida, Kohei</creatorcontrib><creatorcontrib>Okada, Kana</creatorcontrib><creatorcontrib>Mizuno, Serina</creatorcontrib><creatorcontrib>Kato, Asami</creatorcontrib><creatorcontrib>Morimoto, Koji</creatorcontrib><creatorcontrib>Kita, Yasuyuki</creatorcontrib><title>Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes</title><title>Advanced synthesis & catalysis</title><description>The metal‐free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly‐polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings.</description><subject>Arylation</subject><subject>Carboxylic acids</subject><subject>Hypervalent compounds</subject><subject>Iodine</subject><subject>Reactive intermediates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAUhC0EEqWwMnuEIcV2nKQeo5SWSEUdgDly7BfJKImRnQKd6MLOb-wvwRWojEx30rvvpHcIXVIyoYSwG6m9mjBCM0KmPD5CI5rSJOI0FccHn5BTdOb9MwmxaZaN0Mc9DLLdbb_mDgCvgsndppWDsT22DS6kq-37pjUK58poXG-CDuYV8MzIEDRW296su6uyLK9x2Q_gOtBGDuDxAnpwwWls-t3205thjRtnO1wGyFvpwt2fo5NGth4ufnWMnua3j8VdtFwtyiJfRioWLI4gTmUdk0bIRGheEy11o7jSuhZNxjUFAQo0myaMqzRNteCM0ZpTwpNY1UzGYzT56VXOeu-gqV6c6cILFSXVfr5qP191mC8A4gd4My1s_klX-eyh-GO_ARmgeY8</recordid><startdate>20171025</startdate><enddate>20171025</enddate><creator>Dohi, Toshifumi</creator><creator>Koseki, Daichi</creator><creator>Sumida, Kohei</creator><creator>Okada, Kana</creator><creator>Mizuno, Serina</creator><creator>Kato, Asami</creator><creator>Morimoto, Koji</creator><creator>Kita, Yasuyuki</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20171025</creationdate><title>Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes</title><author>Dohi, Toshifumi ; Koseki, Daichi ; Sumida, Kohei ; Okada, Kana ; Mizuno, Serina ; Kato, Asami ; Morimoto, Koji ; Kita, Yasuyuki</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3923-e36ab30f9a59d4b0dadfc4cddb9f74d1e9eced28524c666d94221b410453cb2a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Arylation</topic><topic>Carboxylic acids</topic><topic>Hypervalent compounds</topic><topic>Iodine</topic><topic>Reactive intermediates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dohi, Toshifumi</creatorcontrib><creatorcontrib>Koseki, Daichi</creatorcontrib><creatorcontrib>Sumida, Kohei</creatorcontrib><creatorcontrib>Okada, Kana</creatorcontrib><creatorcontrib>Mizuno, Serina</creatorcontrib><creatorcontrib>Kato, Asami</creatorcontrib><creatorcontrib>Morimoto, Koji</creatorcontrib><creatorcontrib>Kita, Yasuyuki</creatorcontrib><collection>CrossRef</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dohi, Toshifumi</au><au>Koseki, Daichi</au><au>Sumida, Kohei</au><au>Okada, Kana</au><au>Mizuno, Serina</au><au>Kato, Asami</au><au>Morimoto, Koji</au><au>Kita, Yasuyuki</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2017-10-25</date><risdate>2017</risdate><volume>359</volume><issue>20</issue><spage>3503</spage><epage>3508</epage><pages>3503-3508</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The metal‐free arylative coupling of carboxylic acids using iodosoarenes without the use of a catalyst and base, which is applicable to even a highly‐polar molecule bearing multiple alcohol groups, is reported. The in situ preparation of the reactive diaryliodonium(III) carboxylates is the important key to this approach, and the introduction of the trimethoxybenzene auxiliary enables both the smooth salt formations and the selective aryl transfer events during the couplings.</abstract><doi>10.1002/adsc.201700843</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2017-10, Vol.359 (20), p.3503-3508 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_adsc_201700843 |
| source | Access via Wiley Online Library |
| subjects | Arylation Carboxylic acids Hypervalent compounds Iodine Reactive intermediates |
| title | Metal‐Free O‐Arylation of Carboxylic Acid by Active Diaryliodonium(III) Intermediates Generated in situ from Iodosoarenes |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T11%3A50%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-wiley_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Metal%E2%80%90Free%20O%E2%80%90Arylation%20of%20Carboxylic%20Acid%20by%20Active%20Diaryliodonium(III)%20Intermediates%20Generated%20in%E2%80%85situ%20from%20Iodosoarenes&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Dohi,%20Toshifumi&rft.date=2017-10-25&rft.volume=359&rft.issue=20&rft.spage=3503&rft.epage=3508&rft.pages=3503-3508&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201700843&rft_dat=%3Cwiley_cross%3EADSC201700843%3C/wiley_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |