Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin
A general and mild protocol for achieving the carbonylative cross-coupling of sterically hindered, ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered ortho-disubstituted aryl iodide...
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| Veröffentlicht in: | Tetrahedron 2011-06, Vol.67 (24), p.4344-4351 |
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| container_title | Tetrahedron |
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| creator | O’Keefe, B. Michael Simmons, Nicholas Martin, Stephen F. |
| description | A general and mild protocol for achieving the carbonylative cross-coupling of sterically hindered,
ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered
ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl-zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.
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| doi_str_mv | 10.1016/j.tet.2011.03.074 |
| format | Article |
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ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered
ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl-zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.
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ortho-disubstituted aryl ketones is reported. The commercially available PEPPSI-IPr catalyst is shown to efficiently promote the carbonylative cross-coupling of hindered
ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl-zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.
[Display omitted]</description><subject>Aromatic compounds</subject><subject>Arrays</subject><subject>Aryl ketones</subject><subject>Carbon monoxide</subject><subject>Carbonyls</subject><subject>Catalysts</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Cross coupling</subject><subject>iodides</subject><subject>Ketones</subject><subject>luteolin</subject><subject>methodology</subject><subject>N-Heterocyclic carbene</subject><subject>Natural products</subject><subject>Palladium</subject><subject>phosphine</subject><subject>Phosphines</subject><subject>Synthesis (chemistry)</subject><subject>Total synthesis</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqNkk2LFDEQhhtR3HH1B3iRHL10m69O9ygIy-LuCgte9BzSleqdjJlkTDIDc_WXm3HWRS9qIFSSeuolVbxN85LRjlGm3qy7gqXjlLGOio4O8lGzYFLJtpdMPW4WlEraSsrpWfMs5zWlleTiaXPG2cD4UqlF8_3KgPNIDADmTEokuWByYLw_kJULFhNaYtLBk69YYsBM9s4QMGmK4eBNcXskkGLOLcTd1rtw95aYbT1AzcVwVCwrrKEYT_Ih1Et2mcSZ-F3BWAueN09m4zO-uI_nzZerD58vb9rbT9cfLy9uW-hHUVprBi6FVWglQN3czsjMch6NMciHCaCXBmhfn6ntKdCZj1ZJZXFSEudJnDfvT7rb3bRBCxhKMl5vk9vU_nQ0Tv-ZCW6l7-JeC8b5kosq8PpeIMVvO8xFb1wG9N4EjLus2Sj6umTf_xsdpFSDGoT6D5RWSTWMrKLshP4ceML54fOM6qMj9FpXR-ijIzQVujqi1rz6veuHil8WqMC7E4B19nuHSWdwGACtSwhF2-j-Iv8DVdnMGg</recordid><startdate>20110617</startdate><enddate>20110617</enddate><creator>O’Keefe, B. Michael</creator><creator>Simmons, Nicholas</creator><creator>Martin, Stephen F.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7S9</scope><scope>L.6</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20110617</creationdate><title>Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin</title><author>O’Keefe, B. Michael ; Simmons, Nicholas ; Martin, Stephen F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c583t-da7243d6ed4ccd4c2dfe1a9f8aaae27bcc54ac05dfe0d50c0f28d646deb64efb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Aromatic compounds</topic><topic>Arrays</topic><topic>Aryl ketones</topic><topic>Carbon monoxide</topic><topic>Carbonyls</topic><topic>Catalysts</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Cross coupling</topic><topic>iodides</topic><topic>Ketones</topic><topic>luteolin</topic><topic>methodology</topic><topic>N-Heterocyclic carbene</topic><topic>Natural products</topic><topic>Palladium</topic><topic>phosphine</topic><topic>Phosphines</topic><topic>Synthesis (chemistry)</topic><topic>Total synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>O’Keefe, B. Michael</creatorcontrib><creatorcontrib>Simmons, Nicholas</creatorcontrib><creatorcontrib>Martin, Stephen F.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>O’Keefe, B. Michael</au><au>Simmons, Nicholas</au><au>Martin, Stephen F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin</atitle><jtitle>Tetrahedron</jtitle><addtitle>Tetrahedron</addtitle><date>2011-06-17</date><risdate>2011</risdate><volume>67</volume><issue>24</issue><spage>4344</spage><epage>4351</epage><pages>4344-4351</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A general and mild protocol for achieving the carbonylative cross-coupling of sterically hindered,
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ortho-disubstituted aryl iodides to give diaryl ketones; traditional phosphine catalysts are less effective. Carbonylative Suzuki-Miyaura cross-couplings provide a diverse array of biaryl ketones in good to excellent yields. The same catalyst is also shown to catalyze a carbonylative Negishi cross-coupling reaction, utilizing a variety of alkynyl-zinc reagents to give the corresponding alkynyl aryl ketones. Application of this new methodology to the synthesis of the natural product luteolin is reported.
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| ispartof | Tetrahedron, 2011-06, Vol.67 (24), p.4344-4351 |
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| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Aromatic compounds Arrays Aryl ketones Carbon monoxide Carbonyls Catalysts chemical reactions chemical structure Cross coupling iodides Ketones luteolin methodology N-Heterocyclic carbene Natural products Palladium phosphine Phosphines Synthesis (chemistry) Total synthesis |
| title | Facile access to sterically hindered aryl ketones via carbonylative cross-coupling: application to the total synthesis of luteolin |
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