α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism
In the presence of a substoichiometric amount of a tert -butoxy radical precursor, the reaction of alkylamines with sulfonylarenes was found to give α-arylated alkylamines through homolytic aromatic substitution, where a radical chain is operative. A radical chain, conducted by a sulfonyl radical in...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2018-09, Vol.54 (74), p.1471-1474 |
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container_title | Chemical communications (Cambridge, England) |
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creator | Ikeda, Yuko Ueno, Ryota Akai, Yuto Shirakawa, Eiji |
description | In the presence of a substoichiometric amount of a
tert
-butoxy radical precursor, the reaction of alkylamines with sulfonylarenes was found to give α-arylated alkylamines through homolytic aromatic substitution, where a radical chain is operative.
A radical chain, conducted by a sulfonyl radical in a homolytic aromatic substitution mechanism, makes it possible to promote α-arylation of alkylamines with sulfonylarenes just by using a substoichiometric amount of a
tert
-butoxy radical precursor. |
doi_str_mv | 10.1039/c8cc03604g |
format | Article |
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tert
-butoxy radical precursor, the reaction of alkylamines with sulfonylarenes was found to give α-arylated alkylamines through homolytic aromatic substitution, where a radical chain is operative.
A radical chain, conducted by a sulfonyl radical in a homolytic aromatic substitution mechanism, makes it possible to promote α-arylation of alkylamines with sulfonylarenes just by using a substoichiometric amount of a
tert
-butoxy radical precursor.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c8cc03604g</identifier><identifier>PMID: 30156223</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkylamines ; Chains ; Substitution reactions</subject><ispartof>Chemical communications (Cambridge, England), 2018-09, Vol.54 (74), p.1471-1474</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-2fea8e120a020ed7e59e9a848b79b10ee11a5934dc4c5026889e29e8d1e3ed0a3</citedby><cites>FETCH-LOGICAL-c337t-2fea8e120a020ed7e59e9a848b79b10ee11a5934dc4c5026889e29e8d1e3ed0a3</cites><orcidid>0000-0002-8564-984X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30156223$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ikeda, Yuko</creatorcontrib><creatorcontrib>Ueno, Ryota</creatorcontrib><creatorcontrib>Akai, Yuto</creatorcontrib><creatorcontrib>Shirakawa, Eiji</creatorcontrib><title>α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>In the presence of a substoichiometric amount of a
tert
-butoxy radical precursor, the reaction of alkylamines with sulfonylarenes was found to give α-arylated alkylamines through homolytic aromatic substitution, where a radical chain is operative.
A radical chain, conducted by a sulfonyl radical in a homolytic aromatic substitution mechanism, makes it possible to promote α-arylation of alkylamines with sulfonylarenes just by using a substoichiometric amount of a
tert
-butoxy radical precursor.</description><subject>Alkylamines</subject><subject>Chains</subject><subject>Substitution reactions</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkdtKw0AQhhdRbK3eeK8EvBEhusdk97IErUJBBAXvwnYzaVJzqLsJ0sfyRXwmt7ZWcG7-OXwMwz8InRJ8TTBTN0Yag1mE-XwPDQmLeCi4fN1f50KFMeNigI6cW2AfRMhDNGBeI0rZED19fYZju6p0V7ZN0OaBrt58VZcNuOCj7IrA9VXeNr5nYd3rCtv28yLQgdVZaXQVmEKXTVCD16Z09TE6yHXl4GSrI_Ryd_uc3IfTx8lDMp6GhrG4C2kOWgKhWGOKIYtBKFBacjmL1YxgAEK0UIxnhhuBaSSlAqpAZgQYZFizEbrc7F3a9r0H16V16QxUlW6g7V1KsYqEIHEkPHrxD120vW38dSn1DgqsMOGeutpQxrbOWcjTpS1rbVcpwena6DSRSfJj9MTD59uV_ayGbIf-OuuBsw1gndlN_z7FvgEO54Ky</recordid><startdate>20180913</startdate><enddate>20180913</enddate><creator>Ikeda, Yuko</creator><creator>Ueno, Ryota</creator><creator>Akai, Yuto</creator><creator>Shirakawa, Eiji</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/0000-0002-8564-984X</orcidid></search><sort><creationdate>20180913</creationdate><title>α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism</title><author>Ikeda, Yuko ; Ueno, Ryota ; Akai, Yuto ; Shirakawa, Eiji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-2fea8e120a020ed7e59e9a848b79b10ee11a5934dc4c5026889e29e8d1e3ed0a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkylamines</topic><topic>Chains</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ikeda, Yuko</creatorcontrib><creatorcontrib>Ueno, Ryota</creatorcontrib><creatorcontrib>Akai, Yuto</creatorcontrib><creatorcontrib>Shirakawa, Eiji</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>Ikeda, Yuko</au><au>Ueno, Ryota</au><au>Akai, Yuto</au><au>Shirakawa, Eiji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2018-09-13</date><risdate>2018</risdate><volume>54</volume><issue>74</issue><spage>1471</spage><epage>1474</epage><pages>1471-1474</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>In the presence of a substoichiometric amount of a
tert
-butoxy radical precursor, the reaction of alkylamines with sulfonylarenes was found to give α-arylated alkylamines through homolytic aromatic substitution, where a radical chain is operative.
A radical chain, conducted by a sulfonyl radical in a homolytic aromatic substitution mechanism, makes it possible to promote α-arylation of alkylamines with sulfonylarenes just by using a substoichiometric amount of a
tert
-butoxy radical precursor.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30156223</pmid><doi>10.1039/c8cc03604g</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-8564-984X</orcidid></addata></record> |
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ispartof | Chemical communications (Cambridge, England), 2018-09, Vol.54 (74), p.1471-1474 |
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language | eng |
recordid | cdi_proquest_journals_2103509014 |
source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Alkylamines Chains Substitution reactions |
title | α-Arylation of alkylamines with sulfonylarenes through a radical chain mechanism |
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