Iron-Ligand Coordination in Tandem Radical Cyclizations: Synthesis of Benzo[b]thiophenes by a One-pot Reaction of Iron 1,3-Diketone Complexes with 2-Thiosalicylic Acids
Iron—the mediator: 1,3‐Diketone ligands coordinated to iron undergo unprecedented tandem reactions with 2‐thiosalicylic acids to give 2‐substituted 3‐hydroxylbenzo[b]thiophenes in up to 98 % yield. A similar reaction with 2‐mercaptonicotinic acid gave a thieno[2,3‐b]pyridine derivative in 72 % yield...
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| Veröffentlicht in: | Chemistry : a European journal 2011-04, Vol.17 (17), p.4709-4714 |
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| container_issue | 17 |
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| container_title | Chemistry : a European journal |
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| creator | Chan, Sharon Lai-Fung Low, Kam-Hung Yang, Chen Cheung, Samantha Hui-Fung Che, Chi-Ming |
| description | Iron—the mediator: 1,3‐Diketone ligands coordinated to iron undergo unprecedented tandem reactions with 2‐thiosalicylic acids to give 2‐substituted 3‐hydroxylbenzo[b]thiophenes in up to 98 % yield. A similar reaction with 2‐mercaptonicotinic acid gave a thieno[2,3‐b]pyridine derivative in 72 % yield (see scheme). A mechanism involving redox transformation and tandem radical cyclization of the coordinated ligands is proposed. |
| doi_str_mv | 10.1002/chem.201100377 |
| format | Article |
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Eur. J</addtitle><description>Iron—the mediator: 1,3‐Diketone ligands coordinated to iron undergo unprecedented tandem reactions with 2‐thiosalicylic acids to give 2‐substituted 3‐hydroxylbenzo[b]thiophenes in up to 98 % yield. A similar reaction with 2‐mercaptonicotinic acid gave a thieno[2,3‐b]pyridine derivative in 72 % yield (see scheme). A mechanism involving redox transformation and tandem radical cyclization of the coordinated ligands is proposed.</description><subject>Chemistry</subject><subject>coordination complexes</subject><subject>cyclization</subject><subject>iron</subject><subject>Iron - chemistry</subject><subject>Ligands</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemistry</subject><subject>platinum</subject><subject>radical reactions</subject><subject>Salicylates - chemistry</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Thiophenes - chemistry</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkUFv0zAYhiMEYmVw5YgsceBCih3HdsxtdGObKKwqRRwQshznC_WW2CFOtWW_iJ-Ju44KceFgWbaf9_ksvUnynOApwTh7Y9bQTjNM4oEK8SCZEJaRlArOHiYTLHORckblQfIkhEuMseSUPk4OMpJTGslJ8uu89y6d2x_aVWjmfV9ZpwfrHbIOreIltGipK2t0g2ajaezt3Wt4iz6PblhDsAH5Gr0Dd-u_ld-HtfXdGhwEVI5IowsHaecHtARt7qyR3U5E5DVNj-0VDN5BnNt2DdzE0LUd1ihLV1ETdGPNGBc6MrYKT5NHtW4CPLvfD5Mv709Ws7N0fnF6PjuapyYnWKRUal3lRVVIKmumGeOaa8oKUpOal5CLKhcGZzQH0FVJS2kEyzQmGSuZIVrQw-TVztv1_ucGwqBaGww0jXbgN0EVnDBJOS0i-fIf8tJvehc_p4jgnGOaSRmp6Y4yvQ-hh1p1vW11PyqC1bZCta1Q7SuMgRf32k3ZQrXH_3QWAbkDrm0D4390anZ28vFvebrL2jDAzT6r-yvFBRVMff10qsSSLo7xh4Va0N9xo7gz</recordid><startdate>20110418</startdate><enddate>20110418</enddate><creator>Chan, Sharon Lai-Fung</creator><creator>Low, Kam-Hung</creator><creator>Yang, Chen</creator><creator>Cheung, Samantha Hui-Fung</creator><creator>Che, Chi-Ming</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20110418</creationdate><title>Iron-Ligand Coordination in Tandem Radical Cyclizations: Synthesis of Benzo[b]thiophenes by a One-pot Reaction of Iron 1,3-Diketone Complexes with 2-Thiosalicylic Acids</title><author>Chan, Sharon Lai-Fung ; Low, Kam-Hung ; Yang, Chen ; Cheung, Samantha Hui-Fung ; Che, Chi-Ming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4107-39aad48d8939f5a556a6a3581f1f6be47d47c0234eeadb3b9c752a0125b5c1a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Chemistry</topic><topic>coordination complexes</topic><topic>cyclization</topic><topic>iron</topic><topic>Iron - chemistry</topic><topic>Ligands</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemistry</topic><topic>platinum</topic><topic>radical reactions</topic><topic>Salicylates - chemistry</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Thiophenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chan, Sharon Lai-Fung</creatorcontrib><creatorcontrib>Low, Kam-Hung</creatorcontrib><creatorcontrib>Yang, Chen</creatorcontrib><creatorcontrib>Cheung, Samantha Hui-Fung</creatorcontrib><creatorcontrib>Che, Chi-Ming</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chan, Sharon Lai-Fung</au><au>Low, Kam-Hung</au><au>Yang, Chen</au><au>Cheung, Samantha Hui-Fung</au><au>Che, Chi-Ming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Iron-Ligand Coordination in Tandem Radical Cyclizations: Synthesis of Benzo[b]thiophenes by a One-pot Reaction of Iron 1,3-Diketone Complexes with 2-Thiosalicylic Acids</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2011-04-18</date><risdate>2011</risdate><volume>17</volume><issue>17</issue><spage>4709</spage><epage>4714</epage><pages>4709-4714</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Iron—the mediator: 1,3‐Diketone ligands coordinated to iron undergo unprecedented tandem reactions with 2‐thiosalicylic acids to give 2‐substituted 3‐hydroxylbenzo[b]thiophenes in up to 98 % yield. A similar reaction with 2‐mercaptonicotinic acid gave a thieno[2,3‐b]pyridine derivative in 72 % yield (see scheme). A mechanism involving redox transformation and tandem radical cyclization of the coordinated ligands is proposed.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21433152</pmid><doi>10.1002/chem.201100377</doi><tpages>6</tpages></addata></record> |
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| subjects | Chemistry coordination complexes cyclization iron Iron - chemistry Ligands Molecular Structure Organometallic Compounds - chemistry platinum radical reactions Salicylates - chemistry Sulfhydryl Compounds - chemistry Thiophenes - chemistry |
| title | Iron-Ligand Coordination in Tandem Radical Cyclizations: Synthesis of Benzo[b]thiophenes by a One-pot Reaction of Iron 1,3-Diketone Complexes with 2-Thiosalicylic Acids |
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