Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides

A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction,...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2013-12, Vol.15 (24), p.6226-6229
Hauptverfasser:	Shavnya, Andrei, Coffey, Steven B, Smith, Aaron C, Mascitti, Vincent
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Hydrocarbons, Halogenated - chemistry Molecular Structure Organometallic Compounds - chemistry Palladium - chemistry Sulfonamides - chemical synthesis Sulfonamides - chemistry Sulfones - chemical synthesis Sulfones - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

container_end_page	6229
container_issue	24
container_start_page	6226
container_title	Organic letters
container_volume	15
creator	Shavnya, Andrei Coffey, Steven B Smith, Aaron C Mascitti, Vincent
description	A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.
doi_str_mv	10.1021/ol403072r
format	Article
fullrecord	<record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1490746040</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1490746040</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-91bef00538adf54dd21adba803cc46f280ac51795bf9d913b45239b5c8658ca73</originalsourceid><addsrcrecordid>eNptkEtLAzEUhYMotlYX_gHJRtDFaJJJ5uGu1EeFgoK6Hu7kAVMyk5rMLOqvN33Ylav74DsHzkHokpI7Shi9d5aTlOTMH6ExFSxNciLY8WHPyAidhbAkhMZPeYpGjDORCZ6N0fIdrAXVDG0ygx7s-kcr_DFY03TQN67DzuCpX1sMncJz3WvvYHPOwTZKhwf82HgtezyVUoeAe7cVu06HrWJ3QLthz9GJARv0xX5O0Nfz0-dsnizeXl5n00UCaUH7pKS1NoSItABlBFeKUVA1FCSVkmeGFQSkoHkpalOqkqY1jynLWsgiE4WEPJ2gm53vyrvvQYe-apsgdYzZaTeEivKS5DwjsbMJut2h0rsQvDbVyjdtDFhRUm2qrQ7VRvZqbzvUrVYH8q_LCFzvAJChWrrBdzHlP0a_OyWAZw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1490746040</pqid></control><display><type>article</type><title>Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Shavnya, Andrei ; Coffey, Steven B ; Smith, Aaron C ; Mascitti, Vincent</creator><creatorcontrib>Shavnya, Andrei ; Coffey, Steven B ; Smith, Aaron C ; Mascitti, Vincent</creatorcontrib><description>A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol403072r</identifier><identifier>PMID: 24256546</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Hydrocarbons, Halogenated - chemistry ; Molecular Structure ; Organometallic Compounds - chemistry ; Palladium - chemistry ; Sulfonamides - chemical synthesis ; Sulfonamides - chemistry ; Sulfones - chemical synthesis ; Sulfones - chemistry</subject><ispartof>Organic letters, 2013-12, Vol.15 (24), p.6226-6229</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-91bef00538adf54dd21adba803cc46f280ac51795bf9d913b45239b5c8658ca73</citedby><cites>FETCH-LOGICAL-a381t-91bef00538adf54dd21adba803cc46f280ac51795bf9d913b45239b5c8658ca73</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/ol403072r$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol403072r$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24256546$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shavnya, Andrei</creatorcontrib><creatorcontrib>Coffey, Steven B</creatorcontrib><creatorcontrib>Smith, Aaron C</creatorcontrib><creatorcontrib>Mascitti, Vincent</creatorcontrib><title>Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.</description><subject>Catalysis</subject><subject>Hydrocarbons, Halogenated - chemistry</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemistry</subject><subject>Palladium - chemistry</subject><subject>Sulfonamides - chemical synthesis</subject><subject>Sulfonamides - chemistry</subject><subject>Sulfones - chemical synthesis</subject><subject>Sulfones - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEtLAzEUhYMotlYX_gHJRtDFaJJJ5uGu1EeFgoK6Hu7kAVMyk5rMLOqvN33Ylav74DsHzkHokpI7Shi9d5aTlOTMH6ExFSxNciLY8WHPyAidhbAkhMZPeYpGjDORCZ6N0fIdrAXVDG0ygx7s-kcr_DFY03TQN67DzuCpX1sMncJz3WvvYHPOwTZKhwf82HgtezyVUoeAe7cVu06HrWJ3QLthz9GJARv0xX5O0Nfz0-dsnizeXl5n00UCaUH7pKS1NoSItABlBFeKUVA1FCSVkmeGFQSkoHkpalOqkqY1jynLWsgiE4WEPJ2gm53vyrvvQYe-apsgdYzZaTeEivKS5DwjsbMJut2h0rsQvDbVyjdtDFhRUm2qrQ7VRvZqbzvUrVYH8q_LCFzvAJChWrrBdzHlP0a_OyWAZw</recordid><startdate>20131220</startdate><enddate>20131220</enddate><creator>Shavnya, Andrei</creator><creator>Coffey, Steven B</creator><creator>Smith, Aaron C</creator><creator>Mascitti, Vincent</creator><general>American Chemical Society</general><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>20131220</creationdate><title>Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides</title><author>Shavnya, Andrei ; Coffey, Steven B ; Smith, Aaron C ; Mascitti, Vincent</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-91bef00538adf54dd21adba803cc46f280ac51795bf9d913b45239b5c8658ca73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Catalysis</topic><topic>Hydrocarbons, Halogenated - chemistry</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemistry</topic><topic>Palladium - chemistry</topic><topic>Sulfonamides - chemical synthesis</topic><topic>Sulfonamides - chemistry</topic><topic>Sulfones - chemical synthesis</topic><topic>Sulfones - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shavnya, Andrei</creatorcontrib><creatorcontrib>Coffey, Steven B</creatorcontrib><creatorcontrib>Smith, Aaron C</creatorcontrib><creatorcontrib>Mascitti, Vincent</creatorcontrib><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>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shavnya, Andrei</au><au>Coffey, Steven B</au><au>Smith, Aaron C</au><au>Mascitti, Vincent</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2013-12-20</date><risdate>2013</risdate><volume>15</volume><issue>24</issue><spage>6226</spage><epage>6229</epage><pages>6226-6229</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A novel palladium-catalyzed sulfination of aryl and heteroaryl halides is described. This reaction operates under mild conditions and provides access to a wide range of aryl and heteroaryl sulfinates, a useful and versatile class of synthetic intermediates. Capitalizing on this sulfination reaction, one-pot protocols allowing direct access to sulfones and sulfonamides have also been developed. The practicality of these transformations is illustrated with the parallel synthesis of analogues of the drug Viagra.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24256546</pmid><doi>10.1021/ol403072r</doi><tpages>4</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 1523-7060
ispartof	Organic letters, 2013-12, Vol.15 (24), p.6226-6229
issn	1523-7060 1523-7052
language	eng
recordid	cdi_proquest_miscellaneous_1490746040
source	MEDLINE; American Chemical Society Journals
subjects	Catalysis Hydrocarbons, Halogenated - chemistry Molecular Structure Organometallic Compounds - chemistry Palladium - chemistry Sulfonamides - chemical synthesis Sulfonamides - chemistry Sulfones - chemical synthesis Sulfones - chemistry
title	Palladium-Catalyzed Sulfination of Aryl and Heteroaryl Halides: Direct Access to Sulfones and Sulfonamides
url	https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-18T15%3A23%3A14IST&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=Palladium-Catalyzed%20Sulfination%20of%20Aryl%20and%20Heteroaryl%20Halides:%20Direct%20Access%20to%20Sulfones%20and%20Sulfonamides&rft.jtitle=Organic%20letters&rft.au=Shavnya,%20Andrei&rft.date=2013-12-20&rft.volume=15&rft.issue=24&rft.spage=6226&rft.epage=6229&rft.pages=6226-6229&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol403072r&rft_dat=%3Cproquest_cross%3E1490746040%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=1490746040&rft_id=info:pmid/24256546&rfr_iscdi=true