Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group
The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the ol...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2011-05, Vol.76 (9), p.3024-3033 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3033 |
|---|---|
| container_issue | 9 |
| container_start_page | 3024 |
| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Mochida, Satoshi Hirano, Koji Satoh, Tetsuya Miura, Masahiro |
| description | The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives. |
| doi_str_mv | 10.1021/jo200509m |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_864194203</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>864194203</sourcerecordid><originalsourceid>FETCH-LOGICAL-a410t-ace8dd1b357f63f1b024b32faebb6237a8ed5ae30b8a62af34738a2fe87c40c43</originalsourceid><addsrcrecordid>eNpt0E1Lw0AQBuBFFFs_Dv4ByUXEQ3T2I2l6lPqJBUH0HGY3s7qSZOtuItZfb8RaL85lYHh4B17GDjicchD87NULgAymzQYb80xAmk9BbbIxgBCpFLkcsZ0YX2GYLMu22UhwJYtcTMfs7uHFV65v0hl2WC8_qUoe6Nn5SDWZzr1Tcl-TdS12zrfJhQvDdTB6mWAyw6D9x7J2JrkOvl_ssS2LdaT91d5lT1eXj7ObdH5_fTs7n6eoOHQpGiqqimuZTWwuLdcglJbCImmdCznBgqoMSYIuMBdopZrIAoWlYmIUGCV32fFP7iL4t55iVzYuGqprbMn3sSxyxadKgBzkyY80wccYyJaL4BoMy5JD-V1dua5usIer1F43VK3lb1cDOFoBjAZrG7A1Lv45xXkhFPw5NHHI70M7lPHPwy_cPIJk</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>864194203</pqid></control><display><type>article</type><title>Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group</title><source>ACS Publications</source><creator>Mochida, Satoshi ; Hirano, Koji ; Satoh, Tetsuya ; Miura, Masahiro</creator><creatorcontrib>Mochida, Satoshi ; Hirano, Koji ; Satoh, Tetsuya ; Miura, Masahiro</creatorcontrib><description>The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo200509m</identifier><identifier>PMID: 21438629</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Noncondensed benzenic compounds ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2011-05, Vol.76 (9), p.3024-3033</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><rights>2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-ace8dd1b357f63f1b024b32faebb6237a8ed5ae30b8a62af34738a2fe87c40c43</citedby><cites>FETCH-LOGICAL-a410t-ace8dd1b357f63f1b024b32faebb6237a8ed5ae30b8a62af34738a2fe87c40c43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo200509m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo200509m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24118240$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21438629$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mochida, Satoshi</creatorcontrib><creatorcontrib>Hirano, Koji</creatorcontrib><creatorcontrib>Satoh, Tetsuya</creatorcontrib><creatorcontrib>Miura, Masahiro</creatorcontrib><title>Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNpt0E1Lw0AQBuBFFFs_Dv4ByUXEQ3T2I2l6lPqJBUH0HGY3s7qSZOtuItZfb8RaL85lYHh4B17GDjicchD87NULgAymzQYb80xAmk9BbbIxgBCpFLkcsZ0YX2GYLMu22UhwJYtcTMfs7uHFV65v0hl2WC8_qUoe6Nn5SDWZzr1Tcl-TdS12zrfJhQvDdTB6mWAyw6D9x7J2JrkOvl_ssS2LdaT91d5lT1eXj7ObdH5_fTs7n6eoOHQpGiqqimuZTWwuLdcglJbCImmdCznBgqoMSYIuMBdopZrIAoWlYmIUGCV32fFP7iL4t55iVzYuGqprbMn3sSxyxadKgBzkyY80wccYyJaL4BoMy5JD-V1dua5usIer1F43VK3lb1cDOFoBjAZrG7A1Lv45xXkhFPw5NHHI70M7lPHPwy_cPIJk</recordid><startdate>20110506</startdate><enddate>20110506</enddate><creator>Mochida, Satoshi</creator><creator>Hirano, Koji</creator><creator>Satoh, Tetsuya</creator><creator>Miura, Masahiro</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20110506</creationdate><title>Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group</title><author>Mochida, Satoshi ; Hirano, Koji ; Satoh, Tetsuya ; Miura, Masahiro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-ace8dd1b357f63f1b024b32faebb6237a8ed5ae30b8a62af34738a2fe87c40c43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mochida, Satoshi</creatorcontrib><creatorcontrib>Hirano, Koji</creatorcontrib><creatorcontrib>Satoh, Tetsuya</creatorcontrib><creatorcontrib>Miura, Masahiro</creatorcontrib><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mochida, Satoshi</au><au>Hirano, Koji</au><au>Satoh, Tetsuya</au><au>Miura, Masahiro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-05-06</date><risdate>2011</risdate><volume>76</volume><issue>9</issue><spage>3024</spage><epage>3033</epage><pages>3024-3033</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21438629</pmid><doi>10.1021/jo200509m</doi><tpages>10</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2011-05, Vol.76 (9), p.3024-3033 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_864194203 |
| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Noncondensed benzenic compounds Organic chemistry Preparations and properties |
| title | Rhodium-Catalyzed Regioselective Olefination Directed by a Carboxylic Group |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-31T16%3A11%3A40IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Rhodium-Catalyzed%20Regioselective%20Olefination%20Directed%20by%20a%20Carboxylic%20Group&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Mochida,%20Satoshi&rft.date=2011-05-06&rft.volume=76&rft.issue=9&rft.spage=3024&rft.epage=3033&rft.pages=3024-3033&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo200509m&rft_dat=%3Cproquest_cross%3E864194203%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=864194203&rft_id=info:pmid/21438629&rfr_iscdi=true |