Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight
This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylati...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society 2002-04, Vol.124 (14), p.3578-3585 |
|---|---|
| Hauptverfasser: | , , , , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 3585 |
|---|---|
| container_issue | 14 |
| container_start_page | 3578 |
| container_title | Journal of the American Chemical Society |
| container_volume | 124 |
| creator | Martinelli, Michael J Vaidyanathan, Rajappa Pawlak, Joseph M Nayyar, Naresh K Dhokte, Ulhas P Doecke, Christopher W Zollars, Lisa M. H Moher, Eric D Khau, Vien Van Košmrlj, Berta |
| description | This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pK a of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies. |
| doi_str_mv | 10.1021/ja016031r |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_71562593</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>71562593</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-bb5b88259863d501b5efce70381fbd303c4dc1ab9b43c680d083770edc0899bc3</originalsourceid><addsrcrecordid>eNptkMuO0zAUQC0EYkphwQ-gbEBiEfAjjhN2Q8VjpBmB6MDWunZupi5uXOwE0R1bPocf4SP4Ely1mm5YWVc-OvfqEPKY0ReMcvZyDZTVVLB4h8yY5LSUjNd3yYxSykvV1OKMPEhpnceKN-w-OWOs5S2v6hkxCxjB70Zni09440JCj3Z037FYTr4Pw87D6MJQhL7487tcrDDPYDwW596GVfDp1d-fv4qlDVssYOiKK7QrGFzaCy-G5G5W40Nyrwef8NHxnZPPb99cL96Xlx_eXSzOL0sQqh1LY6RpGi7bfG8nKTMSe4uKiob1phNU2KqzDExrKmHrhna0EUpR7Cxt2tZYMSfPDt5tDN8mTKPeuGTRexgwTEkrJuusFxl8fgBtDClF7PU2ug3EnWZU74Pq26CZfXKUTmaD3Yk8FszA0yMAyYLvIwzWpRMnsme_dU7KA5fb4I_bf4hfda2Ekvr641K_VqKS_MuVbk9esEmvwxSH3O4_B_4Dhu-aPw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>71562593</pqid></control><display><type>article</type><title>Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight</title><source>American Chemical Society Publications</source><creator>Martinelli, Michael J ; Vaidyanathan, Rajappa ; Pawlak, Joseph M ; Nayyar, Naresh K ; Dhokte, Ulhas P ; Doecke, Christopher W ; Zollars, Lisa M. H ; Moher, Eric D ; Khau, Vien Van ; Košmrlj, Berta</creator><creatorcontrib>Martinelli, Michael J ; Vaidyanathan, Rajappa ; Pawlak, Joseph M ; Nayyar, Naresh K ; Dhokte, Ulhas P ; Doecke, Christopher W ; Zollars, Lisa M. H ; Moher, Eric D ; Khau, Vien Van ; Košmrlj, Berta</creatorcontrib><description>This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pK a of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja016031r</identifier><identifier>PMID: 11929246</identifier><identifier>CODEN: JACSAT</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Kinetics and mechanisms ; Organic chemistry ; Reactivity and mechanisms</subject><ispartof>Journal of the American Chemical Society, 2002-04, Vol.124 (14), p.3578-3585</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-bb5b88259863d501b5efce70381fbd303c4dc1ab9b43c680d083770edc0899bc3</citedby><cites>FETCH-LOGICAL-a379t-bb5b88259863d501b5efce70381fbd303c4dc1ab9b43c680d083770edc0899bc3</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/ja016031r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ja016031r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=13603259$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11929246$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Martinelli, Michael J</creatorcontrib><creatorcontrib>Vaidyanathan, Rajappa</creatorcontrib><creatorcontrib>Pawlak, Joseph M</creatorcontrib><creatorcontrib>Nayyar, Naresh K</creatorcontrib><creatorcontrib>Dhokte, Ulhas P</creatorcontrib><creatorcontrib>Doecke, Christopher W</creatorcontrib><creatorcontrib>Zollars, Lisa M. H</creatorcontrib><creatorcontrib>Moher, Eric D</creatorcontrib><creatorcontrib>Khau, Vien Van</creatorcontrib><creatorcontrib>Košmrlj, Berta</creatorcontrib><title>Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pK a of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Kinetics and mechanisms</subject><subject>Organic chemistry</subject><subject>Reactivity and mechanisms</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNptkMuO0zAUQC0EYkphwQ-gbEBiEfAjjhN2Q8VjpBmB6MDWunZupi5uXOwE0R1bPocf4SP4Ely1mm5YWVc-OvfqEPKY0ReMcvZyDZTVVLB4h8yY5LSUjNd3yYxSykvV1OKMPEhpnceKN-w-OWOs5S2v6hkxCxjB70Zni09440JCj3Z037FYTr4Pw87D6MJQhL7487tcrDDPYDwW596GVfDp1d-fv4qlDVssYOiKK7QrGFzaCy-G5G5W40Nyrwef8NHxnZPPb99cL96Xlx_eXSzOL0sQqh1LY6RpGi7bfG8nKTMSe4uKiob1phNU2KqzDExrKmHrhna0EUpR7Cxt2tZYMSfPDt5tDN8mTKPeuGTRexgwTEkrJuusFxl8fgBtDClF7PU2ug3EnWZU74Pq26CZfXKUTmaD3Yk8FszA0yMAyYLvIwzWpRMnsme_dU7KA5fb4I_bf4hfda2Ekvr641K_VqKS_MuVbk9esEmvwxSH3O4_B_4Dhu-aPw</recordid><startdate>20020410</startdate><enddate>20020410</enddate><creator>Martinelli, Michael J</creator><creator>Vaidyanathan, Rajappa</creator><creator>Pawlak, Joseph M</creator><creator>Nayyar, Naresh K</creator><creator>Dhokte, Ulhas P</creator><creator>Doecke, Christopher W</creator><creator>Zollars, Lisa M. H</creator><creator>Moher, Eric D</creator><creator>Khau, Vien Van</creator><creator>Košmrlj, Berta</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20020410</creationdate><title>Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight</title><author>Martinelli, Michael J ; Vaidyanathan, Rajappa ; Pawlak, Joseph M ; Nayyar, Naresh K ; Dhokte, Ulhas P ; Doecke, Christopher W ; Zollars, Lisa M. H ; Moher, Eric D ; Khau, Vien Van ; Košmrlj, Berta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-bb5b88259863d501b5efce70381fbd303c4dc1ab9b43c680d083770edc0899bc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Kinetics and mechanisms</topic><topic>Organic chemistry</topic><topic>Reactivity and mechanisms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Martinelli, Michael J</creatorcontrib><creatorcontrib>Vaidyanathan, Rajappa</creatorcontrib><creatorcontrib>Pawlak, Joseph M</creatorcontrib><creatorcontrib>Nayyar, Naresh K</creatorcontrib><creatorcontrib>Dhokte, Ulhas P</creatorcontrib><creatorcontrib>Doecke, Christopher W</creatorcontrib><creatorcontrib>Zollars, Lisa M. H</creatorcontrib><creatorcontrib>Moher, Eric D</creatorcontrib><creatorcontrib>Khau, Vien Van</creatorcontrib><creatorcontrib>Košmrlj, Berta</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Martinelli, Michael J</au><au>Vaidyanathan, Rajappa</au><au>Pawlak, Joseph M</au><au>Nayyar, Naresh K</au><au>Dhokte, Ulhas P</au><au>Doecke, Christopher W</au><au>Zollars, Lisa M. H</au><au>Moher, Eric D</au><au>Khau, Vien Van</au><au>Košmrlj, Berta</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2002-04-10</date><risdate>2002</risdate><volume>124</volume><issue>14</issue><spage>3578</spage><epage>3585</epage><pages>3578-3585</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>This paper describes a convenient protocol for the regioselective sulfonylation of α-chelatable alcohols. Typically, the reaction of α-heterosubstituted alcohols with 1 equiv of p-TsCl and 1 equiv of Et3N in the presence of 2 mol % of Bu2SnO leads to rapid, regioselective, and exclusive monotosylation. The pK a of the amine was correlated to the reaction rate. A plausible mechanism for this reaction has been proposed on the basis of 119Sn NMR studies.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11929246</pmid><doi>10.1021/ja016031r</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0002-7863 |
| ispartof | Journal of the American Chemical Society, 2002-04, Vol.124 (14), p.3578-3585 |
| issn | 0002-7863 1520-5126 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_71562593 |
| source | American Chemical Society Publications |
| subjects | Chemistry Exact sciences and technology Kinetics and mechanisms Organic chemistry Reactivity and mechanisms |
| title | Catalytic Regioselective Sulfonylation of α-Chelatable Alcohols: Scope and Mechanistic Insight |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-20T18%3A56%3A43IST&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=Catalytic%20Regioselective%20Sulfonylation%20of%20%CE%B1-Chelatable%20Alcohols:%E2%80%89%20Scope%20and%20Mechanistic%20Insight&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Martinelli,%20Michael%20J&rft.date=2002-04-10&rft.volume=124&rft.issue=14&rft.spage=3578&rft.epage=3585&rft.pages=3578-3585&rft.issn=0002-7863&rft.eissn=1520-5126&rft.coden=JACSAT&rft_id=info:doi/10.1021/ja016031r&rft_dat=%3Cproquest_cross%3E71562593%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=71562593&rft_id=info:pmid/11929246&rfr_iscdi=true |