Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives
The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate...
Gespeichert in:
| Veröffentlicht in: | Advanced synthesis & catalysis 2021-01, Vol.363 (2), p.464-469 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 469 |
|---|---|
| container_issue | 2 |
| container_start_page | 464 |
| container_title | Advanced synthesis & catalysis |
| container_volume | 363 |
| creator | Deng, Yong You, Shiqi Ruan, Mengyao Wang, Ying Chen, Zuxing Yang, Guichun Gao, Meng |
| description | The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole species, a diverse collection of N1 and C2 phosphorylation products could be obtained in moderate to high yields under exogenous‐oxidant‐free and metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found to be compatible with various alkylamines. |
| doi_str_mv | 10.1002/adsc.202000997 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2478784044</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2478784044</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4207-dbbc9977e9b332ebd5ada97b45c97be87ffeddd1d4d19d7fc5de60594f83301a3</originalsourceid><addsrcrecordid>eNqFkE1OwzAQhS0EEqWwZR2JdYqdOHW8rNJCkSpA_Kwtx560rtK42KEoO47AGTkJjorKks3MaPS-N5qH0CXBI4Jxci21V6MEJxhjztkRGpAxyWJKxvz4MGf4FJ15v8aYsJyxAapnNajWWbWCjVGyjp5gaayHfmt2ED2urN-urOtq2RrbRLaK7k3QL6H5_vwqbNNK05hmGc2hhWDTqRp8JBsdjAICOpqCMzvZm_lzdFLJ2sPFbx-i15vZSzGPFw-3d8VkESuaYBbrslThAwa8TNMESp1JLTkraaZChZxVFWitiaaacM0qlWkY44zTKk9TTGQ6RFd7362zb-_gW7G2764JJ0VCw985xZQG1WivUs5676ASW2c20nWCYNEnKvpExSHRAPA98GFq6P5Ri8n0ufhjfwCt4X74</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2478784044</pqid></control><display><type>article</type><title>Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives</title><source>Wiley Online Library - AutoHoldings Journals</source><creator>Deng, Yong ; You, Shiqi ; Ruan, Mengyao ; Wang, Ying ; Chen, Zuxing ; Yang, Guichun ; Gao, Meng</creator><creatorcontrib>Deng, Yong ; You, Shiqi ; Ruan, Mengyao ; Wang, Ying ; Chen, Zuxing ; Yang, Guichun ; Gao, Meng</creatorcontrib><description>The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole species, a diverse collection of N1 and C2 phosphorylation products could be obtained in moderate to high yields under exogenous‐oxidant‐free and metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found to be compatible with various alkylamines.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202000997</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Alkylamines ; Anodizing ; Derivatives ; Electrochemical Oxidation ; Free Indoles ; N1/C2 Phosphorylation ; Nitrogen ; Oxidation ; Oxidizing agents ; Phosphorylation ; Regioselectivity</subject><ispartof>Advanced synthesis & catalysis, 2021-01, Vol.363 (2), p.464-469</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4207-dbbc9977e9b332ebd5ada97b45c97be87ffeddd1d4d19d7fc5de60594f83301a3</citedby><cites>FETCH-LOGICAL-c4207-dbbc9977e9b332ebd5ada97b45c97be87ffeddd1d4d19d7fc5de60594f83301a3</cites><orcidid>0000-0002-2662-3981</orcidid></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.202000997$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202000997$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Deng, Yong</creatorcontrib><creatorcontrib>You, Shiqi</creatorcontrib><creatorcontrib>Ruan, Mengyao</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Chen, Zuxing</creatorcontrib><creatorcontrib>Yang, Guichun</creatorcontrib><creatorcontrib>Gao, Meng</creatorcontrib><title>Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives</title><title>Advanced synthesis & catalysis</title><description>The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole species, a diverse collection of N1 and C2 phosphorylation products could be obtained in moderate to high yields under exogenous‐oxidant‐free and metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found to be compatible with various alkylamines.</description><subject>Alkylamines</subject><subject>Anodizing</subject><subject>Derivatives</subject><subject>Electrochemical Oxidation</subject><subject>Free Indoles</subject><subject>N1/C2 Phosphorylation</subject><subject>Nitrogen</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Phosphorylation</subject><subject>Regioselectivity</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkE1OwzAQhS0EEqWwZR2JdYqdOHW8rNJCkSpA_Kwtx560rtK42KEoO47AGTkJjorKks3MaPS-N5qH0CXBI4Jxci21V6MEJxhjztkRGpAxyWJKxvz4MGf4FJ15v8aYsJyxAapnNajWWbWCjVGyjp5gaayHfmt2ED2urN-urOtq2RrbRLaK7k3QL6H5_vwqbNNK05hmGc2hhWDTqRp8JBsdjAICOpqCMzvZm_lzdFLJ2sPFbx-i15vZSzGPFw-3d8VkESuaYBbrslThAwa8TNMESp1JLTkraaZChZxVFWitiaaacM0qlWkY44zTKk9TTGQ6RFd7362zb-_gW7G2764JJ0VCw985xZQG1WivUs5676ASW2c20nWCYNEnKvpExSHRAPA98GFq6P5Ri8n0ufhjfwCt4X74</recordid><startdate>20210119</startdate><enddate>20210119</enddate><creator>Deng, Yong</creator><creator>You, Shiqi</creator><creator>Ruan, Mengyao</creator><creator>Wang, Ying</creator><creator>Chen, Zuxing</creator><creator>Yang, Guichun</creator><creator>Gao, Meng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-2662-3981</orcidid></search><sort><creationdate>20210119</creationdate><title>Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives</title><author>Deng, Yong ; You, Shiqi ; Ruan, Mengyao ; Wang, Ying ; Chen, Zuxing ; Yang, Guichun ; Gao, Meng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4207-dbbc9977e9b332ebd5ada97b45c97be87ffeddd1d4d19d7fc5de60594f83301a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alkylamines</topic><topic>Anodizing</topic><topic>Derivatives</topic><topic>Electrochemical Oxidation</topic><topic>Free Indoles</topic><topic>N1/C2 Phosphorylation</topic><topic>Nitrogen</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Phosphorylation</topic><topic>Regioselectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Deng, Yong</creatorcontrib><creatorcontrib>You, Shiqi</creatorcontrib><creatorcontrib>Ruan, Mengyao</creatorcontrib><creatorcontrib>Wang, Ying</creatorcontrib><creatorcontrib>Chen, Zuxing</creatorcontrib><creatorcontrib>Yang, Guichun</creatorcontrib><creatorcontrib>Gao, Meng</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>Deng, Yong</au><au>You, Shiqi</au><au>Ruan, Mengyao</au><au>Wang, Ying</au><au>Chen, Zuxing</au><au>Yang, Guichun</au><au>Gao, Meng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-01-19</date><risdate>2021</risdate><volume>363</volume><issue>2</issue><spage>464</spage><epage>469</epage><pages>464-469</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole species, a diverse collection of N1 and C2 phosphorylation products could be obtained in moderate to high yields under exogenous‐oxidant‐free and metal‐catalyst‐free electrochemical conditions. In addition, N−P coupling was also found to be compatible with various alkylamines.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202000997</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-2662-3981</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1615-4150 |
| ispartof | Advanced synthesis & catalysis, 2021-01, Vol.363 (2), p.464-469 |
| issn | 1615-4150 1615-4169 |
| language | eng |
| recordid | cdi_proquest_journals_2478784044 |
| source | Wiley Online Library - AutoHoldings Journals |
| subjects | Alkylamines Anodizing Derivatives Electrochemical Oxidation Free Indoles N1/C2 Phosphorylation Nitrogen Oxidation Oxidizing agents Phosphorylation Regioselectivity |
| title | Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-03T07%3A40%3A28IST&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=Electrochemical%20Regioselective%20Phosphorylation%20of%20Nitrogen%E2%80%90Containing%20Heterocycles%20and%20Related%20Derivatives&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Deng,%20Yong&rft.date=2021-01-19&rft.volume=363&rft.issue=2&rft.spage=464&rft.epage=469&rft.pages=464-469&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.202000997&rft_dat=%3Cproquest_cross%3E2478784044%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=2478784044&rft_id=info:pmid/&rfr_iscdi=true |