Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates
Complementary palladium-catalyzed methods for direct arylation of oxazole with high regioselectivity (>100:1) at both C-5 and C-2 have been developed for a wide range of aryl and heteroaryl bromides, chlorides, iodides, and triflates. C-5 arylation is preferred in polar solvents with phosphines 5...
Gespeichert in:
| Veröffentlicht in: | Organic letters 2010-08, Vol.12 (16), p.3578-3581 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3581 |
|---|---|
| container_issue | 16 |
| container_start_page | 3578 |
| container_title | Organic letters |
| container_volume | 12 |
| creator | Strotman, Neil A Chobanian, Harry R Guo, Yan He, Jiafang Wilson, Jonathan E |
| description | Complementary palladium-catalyzed methods for direct arylation of oxazole with high regioselectivity (>100:1) at both C-5 and C-2 have been developed for a wide range of aryl and heteroaryl bromides, chlorides, iodides, and triflates. C-5 arylation is preferred in polar solvents with phosphines 5 or 6, whereas C-2 arylation is preferred by nonpolar solvents and phosphine 3. This represents the first general method for C-5 selective arylation of oxazole and should see broad applicability in the synthesis of biologically active molecules. Additionally, potential mechanisms for these two competing arylation processes are proposed on the basis of mechanistic observations. |
| doi_str_mv | 10.1021/ol1011778 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_748946341</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>748946341</sourcerecordid><originalsourceid>FETCH-LOGICAL-a314t-8bb6ea881daa080a82d08782cc1a6363cadb4005f6fccccbb9b4b28f18dfc98f3</originalsourceid><addsrcrecordid>eNptkElLBDEUhIMoLqMH_4DkIiLYmqS39HFsVxBGRM_N6yxOJD3RpFsdT_50o6Nz8l2q4H0UVCG0S8kxJYyeOEsJpWXJV9AmzVmalCRnq0tfkA20FcITiVDOqnW0wUhJsrQqN9HnlXmc2jm-U4_GBWWV6M2rwrdgLUgzdEkNPdj5h5L4zPj4xWM_t9AbN8NO48k7fDirMPS4Thh2PkqO30w__eHwqXedkSoc4XpqnV9YmEl8742OMSpsozUNNqidXx2hh4vz-_oquZlcXtfjmwRSmvUJb9tCAedUAhBOgDNJeMmZEBSKtEgFyDYjJNeFFvHatmqzlnFNudSi4jodoYNF7rN3L4MKfdOZIFSsOVNuCE2Z8Sor0oxG8nBBCu9C8Eo3z9504OcNJc333s1y78ju_aYObafkkvwbOAL7CwBEaJ7c4Gex5D9BX3ush0I</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>748946341</pqid></control><display><type>article</type><title>Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates</title><source>MEDLINE</source><source>ACS Publications</source><creator>Strotman, Neil A ; Chobanian, Harry R ; Guo, Yan ; He, Jiafang ; Wilson, Jonathan E</creator><creatorcontrib>Strotman, Neil A ; Chobanian, Harry R ; Guo, Yan ; He, Jiafang ; Wilson, Jonathan E</creatorcontrib><description>Complementary palladium-catalyzed methods for direct arylation of oxazole with high regioselectivity (>100:1) at both C-5 and C-2 have been developed for a wide range of aryl and heteroaryl bromides, chlorides, iodides, and triflates. C-5 arylation is preferred in polar solvents with phosphines 5 or 6, whereas C-2 arylation is preferred by nonpolar solvents and phosphine 3. This represents the first general method for C-5 selective arylation of oxazole and should see broad applicability in the synthesis of biologically active molecules. Additionally, potential mechanisms for these two competing arylation processes are proposed on the basis of mechanistic observations.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol1011778</identifier><identifier>PMID: 20704397</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Combinatorial Chemistry Techniques ; Hydrocarbons, Brominated - chemistry ; Hydrocarbons, Chlorinated - chemistry ; Mesylates - chemistry ; Molecular Structure ; Oxazoles - chemical synthesis ; Oxazoles - chemistry ; Palladium - chemistry ; Stereoisomerism</subject><ispartof>Organic letters, 2010-08, Vol.12 (16), p.3578-3581</ispartof><rights>Copyright © 2010 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a314t-8bb6ea881daa080a82d08782cc1a6363cadb4005f6fccccbb9b4b28f18dfc98f3</citedby><cites>FETCH-LOGICAL-a314t-8bb6ea881daa080a82d08782cc1a6363cadb4005f6fccccbb9b4b28f18dfc98f3</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/ol1011778$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol1011778$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20704397$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Strotman, Neil A</creatorcontrib><creatorcontrib>Chobanian, Harry R</creatorcontrib><creatorcontrib>Guo, Yan</creatorcontrib><creatorcontrib>He, Jiafang</creatorcontrib><creatorcontrib>Wilson, Jonathan E</creatorcontrib><title>Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Complementary palladium-catalyzed methods for direct arylation of oxazole with high regioselectivity (>100:1) at both C-5 and C-2 have been developed for a wide range of aryl and heteroaryl bromides, chlorides, iodides, and triflates. C-5 arylation is preferred in polar solvents with phosphines 5 or 6, whereas C-2 arylation is preferred by nonpolar solvents and phosphine 3. This represents the first general method for C-5 selective arylation of oxazole and should see broad applicability in the synthesis of biologically active molecules. Additionally, potential mechanisms for these two competing arylation processes are proposed on the basis of mechanistic observations.</description><subject>Catalysis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Hydrocarbons, Brominated - chemistry</subject><subject>Hydrocarbons, Chlorinated - chemistry</subject><subject>Mesylates - chemistry</subject><subject>Molecular Structure</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - chemistry</subject><subject>Palladium - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkElLBDEUhIMoLqMH_4DkIiLYmqS39HFsVxBGRM_N6yxOJD3RpFsdT_50o6Nz8l2q4H0UVCG0S8kxJYyeOEsJpWXJV9AmzVmalCRnq0tfkA20FcITiVDOqnW0wUhJsrQqN9HnlXmc2jm-U4_GBWWV6M2rwrdgLUgzdEkNPdj5h5L4zPj4xWM_t9AbN8NO48k7fDirMPS4Thh2PkqO30w__eHwqXedkSoc4XpqnV9YmEl8742OMSpsozUNNqidXx2hh4vz-_oquZlcXtfjmwRSmvUJb9tCAedUAhBOgDNJeMmZEBSKtEgFyDYjJNeFFvHatmqzlnFNudSi4jodoYNF7rN3L4MKfdOZIFSsOVNuCE2Z8Sor0oxG8nBBCu9C8Eo3z9504OcNJc333s1y78ju_aYObafkkvwbOAL7CwBEaJ7c4Gex5D9BX3ush0I</recordid><startdate>20100820</startdate><enddate>20100820</enddate><creator>Strotman, Neil A</creator><creator>Chobanian, Harry R</creator><creator>Guo, Yan</creator><creator>He, Jiafang</creator><creator>Wilson, Jonathan E</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20100820</creationdate><title>Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates</title><author>Strotman, Neil A ; Chobanian, Harry R ; Guo, Yan ; He, Jiafang ; Wilson, Jonathan E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a314t-8bb6ea881daa080a82d08782cc1a6363cadb4005f6fccccbb9b4b28f18dfc98f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Catalysis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Hydrocarbons, Brominated - chemistry</topic><topic>Hydrocarbons, Chlorinated - chemistry</topic><topic>Mesylates - chemistry</topic><topic>Molecular Structure</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - chemistry</topic><topic>Palladium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Strotman, Neil A</creatorcontrib><creatorcontrib>Chobanian, Harry R</creatorcontrib><creatorcontrib>Guo, Yan</creatorcontrib><creatorcontrib>He, Jiafang</creatorcontrib><creatorcontrib>Wilson, Jonathan E</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Strotman, Neil A</au><au>Chobanian, Harry R</au><au>Guo, Yan</au><au>He, Jiafang</au><au>Wilson, Jonathan E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2010-08-20</date><risdate>2010</risdate><volume>12</volume><issue>16</issue><spage>3578</spage><epage>3581</epage><pages>3578-3581</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Complementary palladium-catalyzed methods for direct arylation of oxazole with high regioselectivity (>100:1) at both C-5 and C-2 have been developed for a wide range of aryl and heteroaryl bromides, chlorides, iodides, and triflates. C-5 arylation is preferred in polar solvents with phosphines 5 or 6, whereas C-2 arylation is preferred by nonpolar solvents and phosphine 3. This represents the first general method for C-5 selective arylation of oxazole and should see broad applicability in the synthesis of biologically active molecules. Additionally, potential mechanisms for these two competing arylation processes are proposed on the basis of mechanistic observations.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>20704397</pmid><doi>10.1021/ol1011778</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2010-08, Vol.12 (16), p.3578-3581 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_748946341 |
| source | MEDLINE; ACS Publications |
| subjects | Catalysis Combinatorial Chemistry Techniques Hydrocarbons, Brominated - chemistry Hydrocarbons, Chlorinated - chemistry Mesylates - chemistry Molecular Structure Oxazoles - chemical synthesis Oxazoles - chemistry Palladium - chemistry Stereoisomerism |
| title | Highly Regioselective Palladium-Catalyzed Direct Arylation of Oxazole at C-2 or C-5 with Aryl Bromides, Chlorides, and Triflates |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-12T15%3A23%3A44IST&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=Highly%20Regioselective%20Palladium-Catalyzed%20Direct%20Arylation%20of%20Oxazole%20at%20C-2%20or%20C-5%20with%20Aryl%20Bromides,%20Chlorides,%20and%20Triflates&rft.jtitle=Organic%20letters&rft.au=Strotman,%20Neil%20A&rft.date=2010-08-20&rft.volume=12&rft.issue=16&rft.spage=3578&rft.epage=3581&rft.pages=3578-3581&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol1011778&rft_dat=%3Cproquest_cross%3E748946341%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=748946341&rft_id=info:pmid/20704397&rfr_iscdi=true |