Direct Synthesis of Sulfonamides and Activated Sulfonate Esters from Sulfonic Acids
A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under hetero...
Gespeichert in:
Veröffentlicht in: | Journal of the American Chemical Society 2004-02, Vol.126 (4), p.1024-1025 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 1025 |
---|---|
container_issue | 4 |
container_start_page | 1024 |
container_title | Journal of the American Chemical Society |
container_volume | 126 |
creator | Caddick, Stephen Wilden, Jonathan D Judd, Duncan B |
description | A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under heterogeneous conditions is also described. These methods provide a fundamentally new approach to making small molecules containing the sulfonamide functional group. |
doi_str_mv | 10.1021/ja0397658 |
format | Article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_80127373</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>80127373</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-7c651d6d96fd6347b3942c992dd446582770542df61bc95c2a164e263eb6c5883</originalsourceid><addsrcrecordid>eNpt0MtuEzEUBmALFdFQWPACaDZFYjHgu8fLENIWEQnQBOjOcmyPcJhL8ZlB5O0xyrTZsLLs8-nX8Y_QC4LfEEzJ273FTCspqkdoQQTFpSBUnqEFxpiWqpLsHD0F2OcrpxV5gs4JV1xySReofh9TcGNRH_rxR4AIxdAU9dQ2Q2-76AMUtvfF0o3xtx2Dvx-NoVjDGBIUTRq6-TW6DKOHZ-hxY1sIz-fzAn29Wm9XN-Xm0_WH1XJTWqb0WConBfHSa9l4ybjaMc2p05p6z3n-DFUKC059I8nOaeGoJZIHKlnYSSeqil2gV8fcuzT8mgKMpovgQtvaPgwTmAoTqphiGb4-QpcGgBQac5diZ9PBEGz-NWgeGsz25Rw67brgT3KuLIPLGVhwtm2S7V2EkxOcEaF1duXRxVzUn4e5TT-NzFsJs_1cm4_f6i-3V---G3zKtQ7MfphSn7v7z4J_ATSNkhs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>80127373</pqid></control><display><type>article</type><title>Direct Synthesis of Sulfonamides and Activated Sulfonate Esters from Sulfonic Acids</title><source>ACS Publications</source><source>MEDLINE</source><creator>Caddick, Stephen ; Wilden, Jonathan D ; Judd, Duncan B</creator><creatorcontrib>Caddick, Stephen ; Wilden, Jonathan D ; Judd, Duncan B</creatorcontrib><description>A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under heterogeneous conditions is also described. These methods provide a fundamentally new approach to making small molecules containing the sulfonamide functional group.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja0397658</identifier><identifier>PMID: 14746462</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Esters - chemistry ; Exact sciences and technology ; Mesylates - chemistry ; Organic chemistry ; Organophosphorus Compounds - chemistry ; Sulfonamides - chemical synthesis ; Sulfonic Acids - chemistry</subject><ispartof>Journal of the American Chemical Society, 2004-02, Vol.126 (4), p.1024-1025</ispartof><rights>Copyright © 2004 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-7c651d6d96fd6347b3942c992dd446582770542df61bc95c2a164e263eb6c5883</citedby><cites>FETCH-LOGICAL-a379t-7c651d6d96fd6347b3942c992dd446582770542df61bc95c2a164e263eb6c5883</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ja0397658$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja0397658$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15431599$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14746462$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Caddick, Stephen</creatorcontrib><creatorcontrib>Wilden, Jonathan D</creatorcontrib><creatorcontrib>Judd, Duncan B</creatorcontrib><title>Direct Synthesis of Sulfonamides and Activated Sulfonate Esters from Sulfonic Acids</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under heterogeneous conditions is also described. These methods provide a fundamentally new approach to making small molecules containing the sulfonamide functional group.</description><subject>Chemistry</subject><subject>Esters - chemistry</subject><subject>Exact sciences and technology</subject><subject>Mesylates - chemistry</subject><subject>Organic chemistry</subject><subject>Organophosphorus Compounds - chemistry</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonic Acids - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MtuEzEUBmALFdFQWPACaDZFYjHgu8fLENIWEQnQBOjOcmyPcJhL8ZlB5O0xyrTZsLLs8-nX8Y_QC4LfEEzJ273FTCspqkdoQQTFpSBUnqEFxpiWqpLsHD0F2OcrpxV5gs4JV1xySReofh9TcGNRH_rxR4AIxdAU9dQ2Q2-76AMUtvfF0o3xtx2Dvx-NoVjDGBIUTRq6-TW6DKOHZ-hxY1sIz-fzAn29Wm9XN-Xm0_WH1XJTWqb0WConBfHSa9l4ybjaMc2p05p6z3n-DFUKC059I8nOaeGoJZIHKlnYSSeqil2gV8fcuzT8mgKMpovgQtvaPgwTmAoTqphiGb4-QpcGgBQac5diZ9PBEGz-NWgeGsz25Rw67brgT3KuLIPLGVhwtm2S7V2EkxOcEaF1duXRxVzUn4e5TT-NzFsJs_1cm4_f6i-3V---G3zKtQ7MfphSn7v7z4J_ATSNkhs</recordid><startdate>20040204</startdate><enddate>20040204</enddate><creator>Caddick, Stephen</creator><creator>Wilden, Jonathan D</creator><creator>Judd, Duncan B</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20040204</creationdate><title>Direct Synthesis of Sulfonamides and Activated Sulfonate Esters from Sulfonic Acids</title><author>Caddick, Stephen ; Wilden, Jonathan D ; Judd, Duncan B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-7c651d6d96fd6347b3942c992dd446582770542df61bc95c2a164e263eb6c5883</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Chemistry</topic><topic>Esters - chemistry</topic><topic>Exact sciences and technology</topic><topic>Mesylates - chemistry</topic><topic>Organic chemistry</topic><topic>Organophosphorus Compounds - chemistry</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonic Acids - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Caddick, Stephen</creatorcontrib><creatorcontrib>Wilden, Jonathan D</creatorcontrib><creatorcontrib>Judd, Duncan B</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Caddick, Stephen</au><au>Wilden, Jonathan D</au><au>Judd, Duncan B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Synthesis of Sulfonamides and Activated Sulfonate Esters from Sulfonic Acids</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2004-02-04</date><risdate>2004</risdate><volume>126</volume><issue>4</issue><spage>1024</spage><epage>1025</epage><pages>1024-1025</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A general new method for the preparation of sulfonamides and activated sulfonate esters by the direct coupling of sulfonic acid salts with amines and alcohols using the reagent triphenylphosphine ditriflate is described. A new reusable polymer-supported reagent for these transformations under heterogeneous conditions is also described. These methods provide a fundamentally new approach to making small molecules containing the sulfonamide functional group.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>14746462</pmid><doi>10.1021/ja0397658</doi><tpages>2</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0002-7863 |
ispartof | Journal of the American Chemical Society, 2004-02, Vol.126 (4), p.1024-1025 |
issn | 0002-7863 1520-5126 |
language | eng |
recordid | cdi_proquest_miscellaneous_80127373 |
source | ACS Publications; MEDLINE |
subjects | Chemistry Esters - chemistry Exact sciences and technology Mesylates - chemistry Organic chemistry Organophosphorus Compounds - chemistry Sulfonamides - chemical synthesis Sulfonic Acids - chemistry |
title | Direct Synthesis of Sulfonamides and Activated Sulfonate Esters from Sulfonic Acids |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-10T18%3A23%3A05IST&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=Direct%20Synthesis%20of%20Sulfonamides%20and%20Activated%20Sulfonate%20Esters%20from%20Sulfonic%20Acids&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Caddick,%20Stephen&rft.date=2004-02-04&rft.volume=126&rft.issue=4&rft.spage=1024&rft.epage=1025&rft.pages=1024-1025&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja0397658&rft_dat=%3Cproquest_cross%3E80127373%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=80127373&rft_id=info:pmid/14746462&rfr_iscdi=true |