New Electrophilic Difluoromethylating Reagent
A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole deriva...
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| Veröffentlicht in: | Organic letters 2007-05, Vol.9 (10), p.1863-1866 |
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| container_end_page | 1866 |
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| container_issue | 10 |
| container_start_page | 1863 |
| container_title | Organic letters |
| container_volume | 9 |
| creator | Prakash, G. K. Surya Weber, Csaba Chacko, Sujith Olah, George A |
| description | A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole derivatives, and phosphines. The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines. |
| doi_str_mv | 10.1021/ol070195g |
| format | Article |
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K. Surya ; Weber, Csaba ; Chacko, Sujith ; Olah, George A</creator><creatorcontrib>Prakash, G. K. Surya ; Weber, Csaba ; Chacko, Sujith ; Olah, George A</creatorcontrib><description>A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole derivatives, and phosphines. The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol070195g</identifier><identifier>PMID: 17444648</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Amines - chemistry ; Boric Acids - chemistry ; Electrons ; Fluorine - chemistry ; Imidazoles - chemistry ; Indicators and Reagents - chemistry ; Methylation ; Molecular Structure ; Nitroimidazoles - chemistry ; Phosphines - chemistry ; Sulfones - chemistry ; Sulfonium Compounds - chemical synthesis ; Sulfonium Compounds - chemistry</subject><ispartof>Organic letters, 2007-05, Vol.9 (10), p.1863-1866</ispartof><rights>Copyright © 2007 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-213609e99ca1082485368e123f386ecccbb9c76f276ae227fb288d37025c8b903</citedby><cites>FETCH-LOGICAL-a379t-213609e99ca1082485368e123f386ecccbb9c76f276ae227fb288d37025c8b903</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/ol070195g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol070195g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17444648$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Prakash, G. 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The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines.</description><subject>Amines - chemistry</subject><subject>Boric Acids - chemistry</subject><subject>Electrons</subject><subject>Fluorine - chemistry</subject><subject>Imidazoles - chemistry</subject><subject>Indicators and Reagents - chemistry</subject><subject>Methylation</subject><subject>Molecular Structure</subject><subject>Nitroimidazoles - chemistry</subject><subject>Phosphines - chemistry</subject><subject>Sulfones - chemistry</subject><subject>Sulfonium Compounds - chemical synthesis</subject><subject>Sulfonium Compounds - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKAzEUQIMotlYX_oB0o-BiNI_Jaym1PqAoiK5DJr3TTslMajKD9O-d0lI3ru7lcjhwD0KXBN8RTMl98FhiovniCA0JpyyTmNPjwy7wAJ2ltMKY9Bd9igZE5nkucjVE2Rv8jKceXBvDeln5yo0fq9J3IYYa2uXG27ZqFuMPsAto2nN0Ulqf4GI_R-jrafo5eclm78-vk4dZZpnUbUYJE1iD1s4SrGiuOBMKCGUlUwKcc0WhnRQllcICpbIsqFJzJjHlThUasxG62XnXMXx3kFpTV8mB97aB0CUjcc6l4lvwdge6GFKKUJp1rGobN4Zgs21jDm169mov7Yoa5n_kPkYPXO8A65JZhS42_Y__iH4BiFJpSg</recordid><startdate>20070510</startdate><enddate>20070510</enddate><creator>Prakash, G. 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Surya ; Weber, Csaba ; Chacko, Sujith ; Olah, George A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-213609e99ca1082485368e123f386ecccbb9c76f276ae227fb288d37025c8b903</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Amines - chemistry</topic><topic>Boric Acids - chemistry</topic><topic>Electrons</topic><topic>Fluorine - chemistry</topic><topic>Imidazoles - chemistry</topic><topic>Indicators and Reagents - chemistry</topic><topic>Methylation</topic><topic>Molecular Structure</topic><topic>Nitroimidazoles - chemistry</topic><topic>Phosphines - chemistry</topic><topic>Sulfones - chemistry</topic><topic>Sulfonium Compounds - chemical synthesis</topic><topic>Sulfonium Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Prakash, G. K. Surya</creatorcontrib><creatorcontrib>Weber, Csaba</creatorcontrib><creatorcontrib>Chacko, Sujith</creatorcontrib><creatorcontrib>Olah, George A</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>Prakash, G. K. Surya</au><au>Weber, Csaba</au><au>Chacko, Sujith</au><au>Olah, George A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Electrophilic Difluoromethylating Reagent</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2007-05-10</date><risdate>2007</risdate><volume>9</volume><issue>10</issue><spage>1863</spage><epage>1866</epage><pages>1863-1866</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A new electrophilic difluoromethylating reagent has been developed. The S-(difluoromethyl)diarylsulfonium tetrafluoroborate has been shown to be effective for the introduction of an electrophilic difluoromethyl group into the following nucleophiles: sulfonic acids, tertiary amines, imidazole derivatives, and phosphines. The reagent failed to transfer the difluoromethyl group to phenols, carbon nucleophiles, and primary and secondary amines.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>17444648</pmid><doi>10.1021/ol070195g</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2007-05, Vol.9 (10), p.1863-1866 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70457850 |
| source | ACS Publications; MEDLINE |
| subjects | Amines - chemistry Boric Acids - chemistry Electrons Fluorine - chemistry Imidazoles - chemistry Indicators and Reagents - chemistry Methylation Molecular Structure Nitroimidazoles - chemistry Phosphines - chemistry Sulfones - chemistry Sulfonium Compounds - chemical synthesis Sulfonium Compounds - chemistry |
| title | New Electrophilic Difluoromethylating Reagent |
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