Electro-oxidative C–H amination of heteroarenes with aniline derivatives via radical–radical cross coupling
The selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated various functionalities with aniline derivatives in a sustainable way remains an unmet challenge. This protocol presents a practical protocol for the C–H amination of heteroarenes via an electro-oxidative cross coupl...
Gespeichert in:
| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2021-11, Vol.23 (22), p.8853-8858 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8858 |
|---|---|
| container_issue | 22 |
| container_start_page | 8853 |
| container_title | Green chemistry : an international journal and green chemistry resource : GC |
| container_volume | 23 |
| creator | Peng, Xichao Zhao, Junhao Ma, Guojian Wu, Yan Hu, Shiyu Ruan, Zhixiong Feng, Pengju |
| description | The selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated various functionalities with aniline derivatives in a sustainable way remains an unmet challenge. This protocol presents a practical protocol for the C–H amination of heteroarenes
via
an electro-oxidative cross coupling process. This electrosynthetic approach enables a facile access to a wide variety of synthetically useful hetero-arene derivatives, tolerates a wide range of functional groups, and is amenable to gram scale synthesis. In addition, a preliminary mechanistic study reveals that a radical cross coupling process between the N-centered radical and indole radical cation may be involved for this amination reaction. |
| doi_str_mv | 10.1039/D1GC02821A |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D1GC02821A</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2597699024</sourcerecordid><originalsourceid>FETCH-LOGICAL-c189t-f12cec1098f105f23693b20797000cae034da8f3b2d908fdbb71e45c124a0c6b3</originalsourceid><addsrcrecordid>eNpFUEtOwzAQtRBIlMKGE1hihxSYcdIkXlahtEiV2MA6cpwxdZXGxU4L7LgDN-QkhLaC1bwZvc_oMXaJcIMQy9s7nBYgcoHjIzbAJI0jKTI4_sOpOGVnISwBELM0GTA3aUh33kXu3daqs1vixffn14yrlW373bXcGb6gjrxTnloK_M12C65a29iWeE3ebne6wLdWca9qq1XTWxwQ196FwLXbrHvByzk7MaoJdHGYQ_Z8P3kqZtH8cfpQjOeRxlx2kUGhSSPI3CCMjIhTGVcCMpkBgFYEcVKr3PS3WkJu6qrKkJKRRpEo0GkVD9nV3nft3euGQlcu3ca3fWQpRjJLpQSR9KzrPWv3pCdTrr1dKf9RIpS_hZb_hcY_FNNrUA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2597699024</pqid></control><display><type>article</type><title>Electro-oxidative C–H amination of heteroarenes with aniline derivatives via radical–radical cross coupling</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Peng, Xichao ; Zhao, Junhao ; Ma, Guojian ; Wu, Yan ; Hu, Shiyu ; Ruan, Zhixiong ; Feng, Pengju</creator><creatorcontrib>Peng, Xichao ; Zhao, Junhao ; Ma, Guojian ; Wu, Yan ; Hu, Shiyu ; Ruan, Zhixiong ; Feng, Pengju</creatorcontrib><description>The selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated various functionalities with aniline derivatives in a sustainable way remains an unmet challenge. This protocol presents a practical protocol for the C–H amination of heteroarenes
via
an electro-oxidative cross coupling process. This electrosynthetic approach enables a facile access to a wide variety of synthetically useful hetero-arene derivatives, tolerates a wide range of functional groups, and is amenable to gram scale synthesis. In addition, a preliminary mechanistic study reveals that a radical cross coupling process between the N-centered radical and indole radical cation may be involved for this amination reaction.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/D1GC02821A</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amination ; Aniline ; Cross coupling ; Functional groups ; Green chemistry ; Synthesis</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2021-11, Vol.23 (22), p.8853-8858</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c189t-f12cec1098f105f23693b20797000cae034da8f3b2d908fdbb71e45c124a0c6b3</citedby><cites>FETCH-LOGICAL-c189t-f12cec1098f105f23693b20797000cae034da8f3b2d908fdbb71e45c124a0c6b3</cites><orcidid>0000-0002-5470-0403 ; 0000-0002-5433-2460</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Peng, Xichao</creatorcontrib><creatorcontrib>Zhao, Junhao</creatorcontrib><creatorcontrib>Ma, Guojian</creatorcontrib><creatorcontrib>Wu, Yan</creatorcontrib><creatorcontrib>Hu, Shiyu</creatorcontrib><creatorcontrib>Ruan, Zhixiong</creatorcontrib><creatorcontrib>Feng, Pengju</creatorcontrib><title>Electro-oxidative C–H amination of heteroarenes with aniline derivatives via radical–radical cross coupling</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>The selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated various functionalities with aniline derivatives in a sustainable way remains an unmet challenge. This protocol presents a practical protocol for the C–H amination of heteroarenes
via
an electro-oxidative cross coupling process. This electrosynthetic approach enables a facile access to a wide variety of synthetically useful hetero-arene derivatives, tolerates a wide range of functional groups, and is amenable to gram scale synthesis. In addition, a preliminary mechanistic study reveals that a radical cross coupling process between the N-centered radical and indole radical cation may be involved for this amination reaction.</description><subject>Amination</subject><subject>Aniline</subject><subject>Cross coupling</subject><subject>Functional groups</subject><subject>Green chemistry</subject><subject>Synthesis</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpFUEtOwzAQtRBIlMKGE1hihxSYcdIkXlahtEiV2MA6cpwxdZXGxU4L7LgDN-QkhLaC1bwZvc_oMXaJcIMQy9s7nBYgcoHjIzbAJI0jKTI4_sOpOGVnISwBELM0GTA3aUh33kXu3daqs1vixffn14yrlW373bXcGb6gjrxTnloK_M12C65a29iWeE3ebne6wLdWca9qq1XTWxwQ196FwLXbrHvByzk7MaoJdHGYQ_Z8P3kqZtH8cfpQjOeRxlx2kUGhSSPI3CCMjIhTGVcCMpkBgFYEcVKr3PS3WkJu6qrKkJKRRpEo0GkVD9nV3nft3euGQlcu3ca3fWQpRjJLpQSR9KzrPWv3pCdTrr1dKf9RIpS_hZb_hcY_FNNrUA</recordid><startdate>20211116</startdate><enddate>20211116</enddate><creator>Peng, Xichao</creator><creator>Zhao, Junhao</creator><creator>Ma, Guojian</creator><creator>Wu, Yan</creator><creator>Hu, Shiyu</creator><creator>Ruan, Zhixiong</creator><creator>Feng, Pengju</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0002-5470-0403</orcidid><orcidid>https://orcid.org/0000-0002-5433-2460</orcidid></search><sort><creationdate>20211116</creationdate><title>Electro-oxidative C–H amination of heteroarenes with aniline derivatives via radical–radical cross coupling</title><author>Peng, Xichao ; Zhao, Junhao ; Ma, Guojian ; Wu, Yan ; Hu, Shiyu ; Ruan, Zhixiong ; Feng, Pengju</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c189t-f12cec1098f105f23693b20797000cae034da8f3b2d908fdbb71e45c124a0c6b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amination</topic><topic>Aniline</topic><topic>Cross coupling</topic><topic>Functional groups</topic><topic>Green chemistry</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peng, Xichao</creatorcontrib><creatorcontrib>Zhao, Junhao</creatorcontrib><creatorcontrib>Ma, Guojian</creatorcontrib><creatorcontrib>Wu, Yan</creatorcontrib><creatorcontrib>Hu, Shiyu</creatorcontrib><creatorcontrib>Ruan, Zhixiong</creatorcontrib><creatorcontrib>Feng, Pengju</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peng, Xichao</au><au>Zhao, Junhao</au><au>Ma, Guojian</au><au>Wu, Yan</au><au>Hu, Shiyu</au><au>Ruan, Zhixiong</au><au>Feng, Pengju</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electro-oxidative C–H amination of heteroarenes with aniline derivatives via radical–radical cross coupling</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2021-11-16</date><risdate>2021</risdate><volume>23</volume><issue>22</issue><spage>8853</spage><epage>8858</epage><pages>8853-8858</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>The selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated various functionalities with aniline derivatives in a sustainable way remains an unmet challenge. This protocol presents a practical protocol for the C–H amination of heteroarenes
via
an electro-oxidative cross coupling process. This electrosynthetic approach enables a facile access to a wide variety of synthetically useful hetero-arene derivatives, tolerates a wide range of functional groups, and is amenable to gram scale synthesis. In addition, a preliminary mechanistic study reveals that a radical cross coupling process between the N-centered radical and indole radical cation may be involved for this amination reaction.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D1GC02821A</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-5470-0403</orcidid><orcidid>https://orcid.org/0000-0002-5433-2460</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2021-11, Vol.23 (22), p.8853-8858 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D1GC02821A |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amination Aniline Cross coupling Functional groups Green chemistry Synthesis |
| title | Electro-oxidative C–H amination of heteroarenes with aniline derivatives via radical–radical cross coupling |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-01T13%3A08%3A43IST&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=Electro-oxidative%20C%E2%80%93H%20amination%20of%20heteroarenes%20with%20aniline%20derivatives%20via%20radical%E2%80%93radical%20cross%20coupling&rft.jtitle=Green%20chemistry%20:%20an%20international%20journal%20and%20green%20chemistry%20resource%20:%20GC&rft.au=Peng,%20Xichao&rft.date=2021-11-16&rft.volume=23&rft.issue=22&rft.spage=8853&rft.epage=8858&rft.pages=8853-8858&rft.issn=1463-9262&rft.eissn=1463-9270&rft_id=info:doi/10.1039/D1GC02821A&rft_dat=%3Cproquest_cross%3E2597699024%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=2597699024&rft_id=info:pmid/&rfr_iscdi=true |