Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex
Single electron oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cy...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2020-05, Vol.362 (11), p.2183-2188 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 2188 |
|---|---|
| container_issue | 11 |
| container_start_page | 2183 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 362 |
| creator | Cho, Yong Hyun Kim, Jae Hyung An, Hyeju Ahn, Kwang‐Hyun Kang, Eun Joo |
| description | Single electron oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first‐row transition metal iron system for the single electron redox reactions. |
| doi_str_mv | 10.1002/adsc.202000191 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2406551079</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2406551079</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3541-d76f509e2ad6ab3ac35887ebca8778594f4214ac664bdd51de53d7a3082a8833</originalsourceid><addsrcrecordid>eNqFkL9OwzAQxi0EEqWwMkdigSHFTuI_GatQIFIlUOnEYl1th7qkcbFbQTcegWfkSUgVVEam-3T3_e5OH0LnBA8Ixsk16KAGCU4wxiQnB6hHGKFxRlh-uNcUH6OTEBathQvOe-i52KragdZ2bV0TTQyonQiRq6Jh_WoaE01AWwV1VEA32QTbvESld81lWZZX359fj3PTQLOee1fbFijcclWbj1N0VEEdzNlv7aPp7Wha3Mfjh7uyGI5jldKMxJqziuLcJKAZzFJou0JwM1PQPihonlVZQjJQjGUzrSnRhqaaQ4pFAkKkaR9ddGtX3r1tTFjLhdv4pr0okwwzSgnmeesadC7lXQjeVHLl7RL8VhIsd_HJXXxyH18L5B3wbmuz_ccthzdPxR_7A8KAdIw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2406551079</pqid></control><display><type>article</type><title>Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Cho, Yong Hyun ; Kim, Jae Hyung ; An, Hyeju ; Ahn, Kwang‐Hyun ; Kang, Eun Joo</creator><creatorcontrib>Cho, Yong Hyun ; Kim, Jae Hyung ; An, Hyeju ; Ahn, Kwang‐Hyun ; Kang, Eun Joo</creatorcontrib><description>Single electron oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first‐row transition metal iron system for the single electron redox reactions.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202000191</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Alkene radical cation ; Alkenes ; Cations ; Cycloaddition ; Cyclopentene ; Cyclopropane ; Electrons ; Iron ; Iron(III)-phenanthroline complex ; Organic compounds ; Oxidation ; Redox reactions ; Single electron oxidation ; Single electrons ; Transition metals</subject><ispartof>Advanced synthesis & catalysis, 2020-05, Vol.362 (11), p.2183-2188</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3541-d76f509e2ad6ab3ac35887ebca8778594f4214ac664bdd51de53d7a3082a8833</citedby><cites>FETCH-LOGICAL-c3541-d76f509e2ad6ab3ac35887ebca8778594f4214ac664bdd51de53d7a3082a8833</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202000191$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202000191$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Cho, Yong Hyun</creatorcontrib><creatorcontrib>Kim, Jae Hyung</creatorcontrib><creatorcontrib>An, Hyeju</creatorcontrib><creatorcontrib>Ahn, Kwang‐Hyun</creatorcontrib><creatorcontrib>Kang, Eun Joo</creatorcontrib><title>Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex</title><title>Advanced synthesis & catalysis</title><description>Single electron oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first‐row transition metal iron system for the single electron redox reactions.</description><subject>Alkene radical cation</subject><subject>Alkenes</subject><subject>Cations</subject><subject>Cycloaddition</subject><subject>Cyclopentene</subject><subject>Cyclopropane</subject><subject>Electrons</subject><subject>Iron</subject><subject>Iron(III)-phenanthroline complex</subject><subject>Organic compounds</subject><subject>Oxidation</subject><subject>Redox reactions</subject><subject>Single electron oxidation</subject><subject>Single electrons</subject><subject>Transition metals</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkL9OwzAQxi0EEqWwMkdigSHFTuI_GatQIFIlUOnEYl1th7qkcbFbQTcegWfkSUgVVEam-3T3_e5OH0LnBA8Ixsk16KAGCU4wxiQnB6hHGKFxRlh-uNcUH6OTEBathQvOe-i52KragdZ2bV0TTQyonQiRq6Jh_WoaE01AWwV1VEA32QTbvESld81lWZZX359fj3PTQLOee1fbFijcclWbj1N0VEEdzNlv7aPp7Wha3Mfjh7uyGI5jldKMxJqziuLcJKAZzFJou0JwM1PQPihonlVZQjJQjGUzrSnRhqaaQ4pFAkKkaR9ddGtX3r1tTFjLhdv4pr0okwwzSgnmeesadC7lXQjeVHLl7RL8VhIsd_HJXXxyH18L5B3wbmuz_ccthzdPxR_7A8KAdIw</recordid><startdate>20200526</startdate><enddate>20200526</enddate><creator>Cho, Yong Hyun</creator><creator>Kim, Jae Hyung</creator><creator>An, Hyeju</creator><creator>Ahn, Kwang‐Hyun</creator><creator>Kang, Eun Joo</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20200526</creationdate><title>Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex</title><author>Cho, Yong Hyun ; Kim, Jae Hyung ; An, Hyeju ; Ahn, Kwang‐Hyun ; Kang, Eun Joo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3541-d76f509e2ad6ab3ac35887ebca8778594f4214ac664bdd51de53d7a3082a8833</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkene radical cation</topic><topic>Alkenes</topic><topic>Cations</topic><topic>Cycloaddition</topic><topic>Cyclopentene</topic><topic>Cyclopropane</topic><topic>Electrons</topic><topic>Iron</topic><topic>Iron(III)-phenanthroline complex</topic><topic>Organic compounds</topic><topic>Oxidation</topic><topic>Redox reactions</topic><topic>Single electron oxidation</topic><topic>Single electrons</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cho, Yong Hyun</creatorcontrib><creatorcontrib>Kim, Jae Hyung</creatorcontrib><creatorcontrib>An, Hyeju</creatorcontrib><creatorcontrib>Ahn, Kwang‐Hyun</creatorcontrib><creatorcontrib>Kang, Eun Joo</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cho, Yong Hyun</au><au>Kim, Jae Hyung</au><au>An, Hyeju</au><au>Ahn, Kwang‐Hyun</au><au>Kang, Eun Joo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2020-05-26</date><risdate>2020</risdate><volume>362</volume><issue>11</issue><spage>2183</spage><epage>2188</epage><pages>2183-2188</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Single electron oxidation of electron‐rich alkenes using the iron(III)‐phenanthroline complex produced electrophilic alkene radical cations, which promoted efficient radical cation [2+1] cycloaddition reactions with diazo compounds. Subsequent chain propagation afforded tri‐ and tetra‐substituted cyclopropanes. This methodology was also expanded to [3+2] cycloaddition reactions with vinyl diazoesters, validating this sustainable, first‐row transition metal iron system for the single electron redox reactions.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202000191</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2020-05, Vol.362 (11), p.2183-2188 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_2406551079 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkene radical cation Alkenes Cations Cycloaddition Cyclopentene Cyclopropane Electrons Iron Iron(III)-phenanthroline complex Organic compounds Oxidation Redox reactions Single electron oxidation Single electrons Transition metals |
| title | Cycloaddition Reactions of Alkene Radical Cations using Iron(III)‐Phenanthroline Complex |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-13T15%3A28%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=Cycloaddition%20Reactions%20of%20Alkene%20Radical%20Cations%20using%20Iron(III)%E2%80%90Phenanthroline%20Complex&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Cho,%20Yong%20Hyun&rft.date=2020-05-26&rft.volume=362&rft.issue=11&rft.spage=2183&rft.epage=2188&rft.pages=2183-2188&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202000191&rft_dat=%3Cproquest_cross%3E2406551079%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=2406551079&rft_id=info:pmid/&rfr_iscdi=true |