Electrochemical sulfinylation of phenols with sulfides: a metal- and oxidant-free cross-coupling for the synthesis of aromatic sulfoxides
The site-selective C-H functionalization of arenes is of indisputable importance in organic chemistry. Herein, we have demonstrated an electrochemical regioselective oxidative cross-coupling towards the direct C(sp 2 )-H sulfinylation of phenols with sulfides under mild reaction conditions. The desi...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2023-01, Vol.59 (3), p.31-313 |
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creator | Kumar, Rakesh Taily, Irshad Maajid Banerjee, Prabal |
description | The site-selective C-H functionalization of arenes is of indisputable importance in organic chemistry. Herein, we have demonstrated an electrochemical regioselective oxidative cross-coupling towards the direct C(sp
2
)-H sulfinylation of phenols with sulfides under mild reaction conditions. The designed methodology furnished aryl sulfoxides in good to moderate yields under exogenous metal and oxidant-free conditions. Moreover, the exploitation of traceless electrons to carry out the tandem site-selective oxidative aryl chalcogenation is the striking feature of this methodology.
Electrochemical site-selective sulfinylation of phenol. |
doi_str_mv | 10.1039/d2cc05207e |
format | Article |
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2
)-H sulfinylation of phenols with sulfides under mild reaction conditions. The designed methodology furnished aryl sulfoxides in good to moderate yields under exogenous metal and oxidant-free conditions. Moreover, the exploitation of traceless electrons to carry out the tandem site-selective oxidative aryl chalcogenation is the striking feature of this methodology.
Electrochemical site-selective sulfinylation of phenol.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d2cc05207e</identifier><identifier>PMID: 36507914</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Cross coupling ; Organic chemistry ; Oxidizing agents ; Phenols ; Sulfides ; Sulfoxides</subject><ispartof>Chemical communications (Cambridge, England), 2023-01, Vol.59 (3), p.31-313</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-3a22dbff919cef47c9f19b06a0b2d908ada79d87638e6ec2d709672c553acf863</citedby><cites>FETCH-LOGICAL-c337t-3a22dbff919cef47c9f19b06a0b2d908ada79d87638e6ec2d709672c553acf863</cites><orcidid>0000-0002-3569-7624</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36507914$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kumar, Rakesh</creatorcontrib><creatorcontrib>Taily, Irshad Maajid</creatorcontrib><creatorcontrib>Banerjee, Prabal</creatorcontrib><title>Electrochemical sulfinylation of phenols with sulfides: a metal- and oxidant-free cross-coupling for the synthesis of aromatic sulfoxides</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The site-selective C-H functionalization of arenes is of indisputable importance in organic chemistry. Herein, we have demonstrated an electrochemical regioselective oxidative cross-coupling towards the direct C(sp
2
)-H sulfinylation of phenols with sulfides under mild reaction conditions. The designed methodology furnished aryl sulfoxides in good to moderate yields under exogenous metal and oxidant-free conditions. Moreover, the exploitation of traceless electrons to carry out the tandem site-selective oxidative aryl chalcogenation is the striking feature of this methodology.
Electrochemical site-selective sulfinylation of phenol.</description><subject>Aromatic compounds</subject><subject>Cross coupling</subject><subject>Organic chemistry</subject><subject>Oxidizing agents</subject><subject>Phenols</subject><subject>Sulfides</subject><subject>Sulfoxides</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkU2LFDEQhoMo7odevCsBL4vQaz46SWdvMo66sLAXBW9NJqk4WdLJmHSj8xP819s9s65gXaqgnnqrihehV5RcUsL1e8esJYIRBU_QKeWybUTbfX-61EI3irfiBJ3VekfmoKJ7jk64FERp2p6iP-sIdizZbmEI1kRcp-hD2kczhpxw9ni3hZRjxb_CuD12HdQrbPAAo4kNNsnh_Ds4k8bGFwBsS661sXnaxZB-YJ8LHreA6z7NqYa6iJqSh3mDPQgu01BfoGfexAovH_I5-vZp_XX1pbm5_Xy9-nDTWM7V2HDDmNt4r6m24Ftltad6Q6QhG-Y06YwzSrtOSd6BBMucIloqZoXgxvpO8nN0cdTdlfxzgjr2Q6gWYjQJ8lR7pgSXUnZKzejb_9C7PJU0XzdTkhBJKV-od0fq8HgB3-9KGEzZ95T0i0H9R7ZaHQxaz_CbB8lpM4B7RP86MgOvj0Cp9rH7z2F-D-49l6Y</recordid><startdate>20230103</startdate><enddate>20230103</enddate><creator>Kumar, Rakesh</creator><creator>Taily, Irshad Maajid</creator><creator>Banerjee, Prabal</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3569-7624</orcidid></search><sort><creationdate>20230103</creationdate><title>Electrochemical sulfinylation of phenols with sulfides: a metal- and oxidant-free cross-coupling for the synthesis of aromatic sulfoxides</title><author>Kumar, Rakesh ; Taily, Irshad Maajid ; Banerjee, Prabal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-3a22dbff919cef47c9f19b06a0b2d908ada79d87638e6ec2d709672c553acf863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aromatic compounds</topic><topic>Cross coupling</topic><topic>Organic chemistry</topic><topic>Oxidizing agents</topic><topic>Phenols</topic><topic>Sulfides</topic><topic>Sulfoxides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumar, Rakesh</creatorcontrib><creatorcontrib>Taily, Irshad Maajid</creatorcontrib><creatorcontrib>Banerjee, Prabal</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumar, Rakesh</au><au>Taily, Irshad Maajid</au><au>Banerjee, Prabal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical sulfinylation of phenols with sulfides: a metal- and oxidant-free cross-coupling for the synthesis of aromatic sulfoxides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2023-01-03</date><risdate>2023</risdate><volume>59</volume><issue>3</issue><spage>31</spage><epage>313</epage><pages>31-313</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The site-selective C-H functionalization of arenes is of indisputable importance in organic chemistry. Herein, we have demonstrated an electrochemical regioselective oxidative cross-coupling towards the direct C(sp
2
)-H sulfinylation of phenols with sulfides under mild reaction conditions. The designed methodology furnished aryl sulfoxides in good to moderate yields under exogenous metal and oxidant-free conditions. Moreover, the exploitation of traceless electrons to carry out the tandem site-selective oxidative aryl chalcogenation is the striking feature of this methodology.
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source | Alma/SFX Local Collection; Royal Society of Chemistry E-Journals |
subjects | Aromatic compounds Cross coupling Organic chemistry Oxidizing agents Phenols Sulfides Sulfoxides |
title | Electrochemical sulfinylation of phenols with sulfides: a metal- and oxidant-free cross-coupling for the synthesis of aromatic sulfoxides |
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