Arylation and alkenylation of activated alkyl halides using sulfonamides
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S N 2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-C aryl bond under simple conditions...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2020-03, Vol.56 (21), p.3222-3224 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Johnson, Stuart Kovács, Ervin Greaney, Michael F |
| description | A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-C
aryl
bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. |
| doi_str_mv | 10.1039/d0cc00220h |
| format | Article |
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N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-C
aryl
bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d0cc00220h</identifier><identifier>PMID: 32073052</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aromatic compounds ; Carbonyl compounds ; Carbonyls ; Chemical synthesis ; Crystallography ; Derivatives ; Extrusion ; Halides ; Harnesses ; Organometallic compounds ; Sulfonamides ; Sulfur dioxide ; Transition metals</subject><ispartof>Chemical communications (Cambridge, England), 2020-03, Vol.56 (21), p.3222-3224</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c465t-abbd1b9e473d83f6afa2b7a281e98ac87ec3b68782f59149ac777bfbad39ff953</citedby><cites>FETCH-LOGICAL-c465t-abbd1b9e473d83f6afa2b7a281e98ac87ec3b68782f59149ac777bfbad39ff953</cites><orcidid>0000-0001-9633-1135 ; 0000-0002-3939-6925</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32073052$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Johnson, Stuart</creatorcontrib><creatorcontrib>Kovács, Ervin</creatorcontrib><creatorcontrib>Greaney, Michael F</creatorcontrib><title>Arylation and alkenylation of activated alkyl halides using sulfonamides</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-C
aryl
bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds.</description><subject>Aromatic compounds</subject><subject>Carbonyl compounds</subject><subject>Carbonyls</subject><subject>Chemical synthesis</subject><subject>Crystallography</subject><subject>Derivatives</subject><subject>Extrusion</subject><subject>Halides</subject><subject>Harnesses</subject><subject>Organometallic compounds</subject><subject>Sulfonamides</subject><subject>Sulfur dioxide</subject><subject>Transition metals</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kU1LxDAQhoMorq5evCsVLyJU06RpkuNSP1ZY8KLgrUzTxO3abdekFfbfm-6X4MG5zDDvM8PwDkJnEb6NMJV3BVYKY0LwdA8dRTSJQxaL9_2-ZjLkNGYDdOzcDPuImDhEA0owp5iRIzQe2WUFbdnUAdRFANWnrreNxgSg2vIbWr1SllUwhaostAs6V9Yfgesq09Qw71sn6MBA5fTpJg_R2-PDazoOJy9Pz-loEqo4YW0IeV5EudQxp4WgJgEDJOdARKSlACW4VjRPBBfEMBnFEhTnPDc5FFQaIxkdouv13oVtvjrt2mxeOqWrCmrddC4jlAnmx3mPXv1BZ01na3-dp3jinSKx9NTNmlK2cc5qky1sOQe7zCKc9f5m9zhNV_6OPXyxWdnlc13s0K2hHjhfA9apnfr7IK9f_qdni8LQHzqLito</recordid><startdate>20200312</startdate><enddate>20200312</enddate><creator>Johnson, Stuart</creator><creator>Kovács, Ervin</creator><creator>Greaney, Michael F</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/0000-0001-9633-1135</orcidid><orcidid>https://orcid.org/0000-0002-3939-6925</orcidid></search><sort><creationdate>20200312</creationdate><title>Arylation and alkenylation of activated alkyl halides using sulfonamides</title><author>Johnson, Stuart ; Kovács, Ervin ; Greaney, Michael F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c465t-abbd1b9e473d83f6afa2b7a281e98ac87ec3b68782f59149ac777bfbad39ff953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aromatic compounds</topic><topic>Carbonyl compounds</topic><topic>Carbonyls</topic><topic>Chemical synthesis</topic><topic>Crystallography</topic><topic>Derivatives</topic><topic>Extrusion</topic><topic>Halides</topic><topic>Harnesses</topic><topic>Organometallic compounds</topic><topic>Sulfonamides</topic><topic>Sulfur dioxide</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Johnson, Stuart</creatorcontrib><creatorcontrib>Kovács, Ervin</creatorcontrib><creatorcontrib>Greaney, Michael F</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>Johnson, Stuart</au><au>Kovács, Ervin</au><au>Greaney, Michael F</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Arylation and alkenylation of activated alkyl halides using sulfonamides</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2020-03-12</date><risdate>2020</risdate><volume>56</volume><issue>21</issue><spage>3222</spage><epage>3224</epage><pages>3222-3224</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-C
aryl
bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl sulfonamides, producing sterically congested quaternary alkene amino acid derivatives.
A variety of quaternary aryl amino acid derivatives can be synthesised using tandem S
N
2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32073052</pmid><doi>10.1039/d0cc00220h</doi><tpages>3</tpages><orcidid>https://orcid.org/0000-0001-9633-1135</orcidid><orcidid>https://orcid.org/0000-0002-3939-6925</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2020-03, Vol.56 (21), p.3222-3224 |
| issn | 1359-7345 1364-548X |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aromatic compounds Carbonyl compounds Carbonyls Chemical synthesis Crystallography Derivatives Extrusion Halides Harnesses Organometallic compounds Sulfonamides Sulfur dioxide Transition metals |
| title | Arylation and alkenylation of activated alkyl halides using sulfonamides |
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