Synthetic Routes to 5,10,15-Triaryl-tetrabenzocorroles
Two different synthetic routes for the preparation of 5,10,15-triaryl-tetrabenzocorroles have been developed. The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole an...
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| Veröffentlicht in: | Journal of organic chemistry 2011-05, Vol.76 (10), p.3765-3773 |
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| container_end_page | 3773 |
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| container_issue | 10 |
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| container_title | Journal of organic chemistry |
| container_volume | 76 |
| creator | Pomarico, Giuseppe Nardis, Sara Paolesse, Roberto Ongayi, Owendi C Courtney, Brandy H Fronczek, Frank R Vicente, Maria Graça H |
| description | Two different synthetic routes for the preparation of 5,10,15-triaryl-tetrabenzocorroles have been developed. The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole and a suitable substrate to form the four β-fused aryl rings. These routes are successful to lead to the target tetrabenzocorroles, obtained in both cases as the corresponding Cu complex and with the highest yield obtained via the one-step cross-coupling methodology. Demetalation of the Cu-tetrabenzocorrole produces the corresponding free base; this macrocycle was further exploited to obtain the Sn and Co complexes in good yields. |
| doi_str_mv | 10.1021/jo200026u |
| format | Article |
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The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole and a suitable substrate to form the four β-fused aryl rings. These routes are successful to lead to the target tetrabenzocorroles, obtained in both cases as the corresponding Cu complex and with the highest yield obtained via the one-step cross-coupling methodology. Demetalation of the Cu-tetrabenzocorrole produces the corresponding free base; this macrocycle was further exploited to obtain the Sn and Co complexes in good yields.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo200026u</identifier><identifier>PMID: 21480644</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 only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Organic chemistry ; Organometallic Compounds - chemistry ; Porphyrins - chemical synthesis ; Porphyrins - chemistry ; Preparations and properties ; Spectrophotometry, Ultraviolet</subject><ispartof>Journal of organic chemistry, 2011-05, Vol.76 (10), p.3765-3773</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-f01ca3e3a6210d0defb765a5b0148994800c05fee74ea0e77d15525b225674b13</citedby><cites>FETCH-LOGICAL-a410t-f01ca3e3a6210d0defb765a5b0148994800c05fee74ea0e77d15525b225674b13</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/jo200026u$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo200026u$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27080,27928,27929,56742,56792</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24158184$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21480644$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pomarico, Giuseppe</creatorcontrib><creatorcontrib>Nardis, Sara</creatorcontrib><creatorcontrib>Paolesse, Roberto</creatorcontrib><creatorcontrib>Ongayi, Owendi C</creatorcontrib><creatorcontrib>Courtney, Brandy H</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Vicente, Maria Graça H</creatorcontrib><title>Synthetic Routes to 5,10,15-Triaryl-tetrabenzocorroles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Two different synthetic routes for the preparation of 5,10,15-triaryl-tetrabenzocorroles have been developed. The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole and a suitable substrate to form the four β-fused aryl rings. These routes are successful to lead to the target tetrabenzocorroles, obtained in both cases as the corresponding Cu complex and with the highest yield obtained via the one-step cross-coupling methodology. Demetalation of the Cu-tetrabenzocorrole produces the corresponding free base; this macrocycle was further exploited to obtain the Sn and Co complexes in good yields.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Organic chemistry</subject><subject>Organometallic Compounds - chemistry</subject><subject>Porphyrins - chemical synthesis</subject><subject>Porphyrins - chemistry</subject><subject>Preparations and properties</subject><subject>Spectrophotometry, Ultraviolet</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E9LwzAYBvAgipvTg19AdhERVn3fNEnXowz_wUDQeS5p-hY7ukaT9DA_vZHN6cFTIPzy5OFh7BThCoHj9dJyAOCq32NDlBwSlYPYZ8N4x5OUq3TAjrxfRgNSykM24CimoIQYMvWy7sIbhcaMn20fyI-DHcsJwgRlsnCNdus2CRScLqn7tMY6Z1vyx-yg1q2nk-05Yq93t4vZQzJ_un-c3cwTLRBCUgManVKqFUeooKK6zJTUsoRYIM9jCTAga6JMkAbKsgql5LLkXKpMlJiO2MUm993Zj558KFaNN9S2uiPb-2KaCZ7n8UmUlxtpnPXeUV28u2YV6xcIxfdKxW6laM-2qX25omonf2aJ4HwLtDe6rZ3uTON_nUA5xekfp42P-b3r4hj_fPgFWRZ4lA</recordid><startdate>20110520</startdate><enddate>20110520</enddate><creator>Pomarico, Giuseppe</creator><creator>Nardis, Sara</creator><creator>Paolesse, Roberto</creator><creator>Ongayi, Owendi C</creator><creator>Courtney, Brandy H</creator><creator>Fronczek, Frank R</creator><creator>Vicente, Maria Graça H</creator><general>American Chemical Society</general><scope>IQODW</scope><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>20110520</creationdate><title>Synthetic Routes to 5,10,15-Triaryl-tetrabenzocorroles</title><author>Pomarico, Giuseppe ; Nardis, Sara ; Paolesse, Roberto ; Ongayi, Owendi C ; Courtney, Brandy H ; Fronczek, Frank R ; Vicente, Maria Graça H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-f01ca3e3a6210d0defb765a5b0148994800c05fee74ea0e77d15525b225674b13</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 only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Organic chemistry</topic><topic>Organometallic Compounds - chemistry</topic><topic>Porphyrins - chemical synthesis</topic><topic>Porphyrins - chemistry</topic><topic>Preparations and properties</topic><topic>Spectrophotometry, Ultraviolet</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pomarico, Giuseppe</creatorcontrib><creatorcontrib>Nardis, Sara</creatorcontrib><creatorcontrib>Paolesse, Roberto</creatorcontrib><creatorcontrib>Ongayi, Owendi C</creatorcontrib><creatorcontrib>Courtney, Brandy H</creatorcontrib><creatorcontrib>Fronczek, Frank R</creatorcontrib><creatorcontrib>Vicente, Maria Graça H</creatorcontrib><collection>Pascal-Francis</collection><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>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pomarico, Giuseppe</au><au>Nardis, Sara</au><au>Paolesse, Roberto</au><au>Ongayi, Owendi C</au><au>Courtney, Brandy H</au><au>Fronczek, Frank R</au><au>Vicente, Maria Graça H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthetic Routes to 5,10,15-Triaryl-tetrabenzocorroles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2011-05-20</date><risdate>2011</risdate><volume>76</volume><issue>10</issue><spage>3765</spage><epage>3773</epage><pages>3765-3773</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>Two different synthetic routes for the preparation of 5,10,15-triaryl-tetrabenzocorroles have been developed. The first approach is based on the condensation of a tetrahydroisoindole with aryl-aldehydes, and the second pathway involves a cross-coupling reaction between a bromo-substituted corrole and a suitable substrate to form the four β-fused aryl rings. These routes are successful to lead to the target tetrabenzocorroles, obtained in both cases as the corresponding Cu complex and with the highest yield obtained via the one-step cross-coupling methodology. Demetalation of the Cu-tetrabenzocorrole produces the corresponding free base; this macrocycle was further exploited to obtain the Sn and Co complexes in good yields.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>21480644</pmid><doi>10.1021/jo200026u</doi><tpages>9</tpages></addata></record> |
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| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Organic chemistry Organometallic Compounds - chemistry Porphyrins - chemical synthesis Porphyrins - chemistry Preparations and properties Spectrophotometry, Ultraviolet |
| title | Synthetic Routes to 5,10,15-Triaryl-tetrabenzocorroles |
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