NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions
An organo-catalytic protocol for the trimethylsilylation of terminal alkynes employing Ruppert's reagent (CF 3 SiMe 3 ) as a trimethylsilyl source has been developed under solvent and fluoride free conditions. This method was found to be very effective as a variety of terminal alkynes bearing a...
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| Veröffentlicht in: | RSC advances 2014-01, Vol.4 (91), p.49775-49779 |
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| container_issue | 91 |
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| container_title | RSC advances |
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| creator | Arde, Panjab Reddy, Virsinha Vijaya Anand, Ramasamy |
| description | An organo-catalytic protocol for the trimethylsilylation of terminal alkynes employing Ruppert's reagent (CF
3
SiMe
3
) as a trimethylsilyl source has been developed under solvent and fluoride free conditions. This method was found to be very effective as a variety of terminal alkynes bearing aliphatic or aromatic substituents underwent smooth transformation to their corresponding silylated products in excellent yields within a few minutes using N-heterocyclic carbene as an organo-catalyst. This methodology was also applied to the chemospecific N-silylation of indoles. |
| doi_str_mv | 10.1039/C4RA08727E |
| format | Article |
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3
SiMe
3
) as a trimethylsilyl source has been developed under solvent and fluoride free conditions. This method was found to be very effective as a variety of terminal alkynes bearing aliphatic or aromatic substituents underwent smooth transformation to their corresponding silylated products in excellent yields within a few minutes using N-heterocyclic carbene as an organo-catalyst. This methodology was also applied to the chemospecific N-silylation of indoles.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/C4RA08727E</identifier><language>eng</language><subject>Aliphatic compounds ; Alkynes ; Carbenes ; Indoles ; Solvents ; Terminals ; Transformations ; Trimethylsilylation</subject><ispartof>RSC advances, 2014-01, Vol.4 (91), p.49775-49779</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c264t-c470b0fba3b60355c82a6520d94ded22a88e536c34a1cdb0dd058b9af49463d93</citedby><cites>FETCH-LOGICAL-c264t-c470b0fba3b60355c82a6520d94ded22a88e536c34a1cdb0dd058b9af49463d93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Arde, Panjab</creatorcontrib><creatorcontrib>Reddy, Virsinha</creatorcontrib><creatorcontrib>Vijaya Anand, Ramasamy</creatorcontrib><title>NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions</title><title>RSC advances</title><description>An organo-catalytic protocol for the trimethylsilylation of terminal alkynes employing Ruppert's reagent (CF
3
SiMe
3
) as a trimethylsilyl source has been developed under solvent and fluoride free conditions. This method was found to be very effective as a variety of terminal alkynes bearing aliphatic or aromatic substituents underwent smooth transformation to their corresponding silylated products in excellent yields within a few minutes using N-heterocyclic carbene as an organo-catalyst. This methodology was also applied to the chemospecific N-silylation of indoles.</description><subject>Aliphatic compounds</subject><subject>Alkynes</subject><subject>Carbenes</subject><subject>Indoles</subject><subject>Solvents</subject><subject>Terminals</subject><subject>Transformations</subject><subject>Trimethylsilylation</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNpNkEFLwzAcxYsoOOYufoLcFKGaJmnaHkeZThCFoeeSJv-6aJbUJJ3029sxQd_lvQePd_glyWWGbzNMq7uabZa4LEixOklmBDOeEsyr03_5PFmE8IEn8TwjPJsl--d1jaSIwowBFIpe7yBuRxO0GY2I2lnkOhTB77QVBgnzOVoISFiFtFXOTPlbxy3aDH0PPl4F5EG8g41osAo8Cs7sD63zAEg6q_ThM1wkZ50wARa_Pk_e7lev9Tp9enl4rJdPqSScxVSyAre4awVtOaZ5LksieE6wqpgCRYgoS8gpl5SJTKoWK4Xzsq1ExyrGqaroPLk-_vbefQ0QYrPTQYIxwoIbQpNNHGhRFpxN05vjVHoXgoeu6ScYwo9NhpsD3-aPL_0BcWdvcA</recordid><startdate>20140101</startdate><enddate>20140101</enddate><creator>Arde, Panjab</creator><creator>Reddy, Virsinha</creator><creator>Vijaya Anand, Ramasamy</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20140101</creationdate><title>NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions</title><author>Arde, Panjab ; Reddy, Virsinha ; Vijaya Anand, Ramasamy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c264t-c470b0fba3b60355c82a6520d94ded22a88e536c34a1cdb0dd058b9af49463d93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Aliphatic compounds</topic><topic>Alkynes</topic><topic>Carbenes</topic><topic>Indoles</topic><topic>Solvents</topic><topic>Terminals</topic><topic>Transformations</topic><topic>Trimethylsilylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Arde, Panjab</creatorcontrib><creatorcontrib>Reddy, Virsinha</creatorcontrib><creatorcontrib>Vijaya Anand, Ramasamy</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Arde, Panjab</au><au>Reddy, Virsinha</au><au>Vijaya Anand, Ramasamy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions</atitle><jtitle>RSC advances</jtitle><date>2014-01-01</date><risdate>2014</risdate><volume>4</volume><issue>91</issue><spage>49775</spage><epage>49779</epage><pages>49775-49779</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>An organo-catalytic protocol for the trimethylsilylation of terminal alkynes employing Ruppert's reagent (CF
3
SiMe
3
) as a trimethylsilyl source has been developed under solvent and fluoride free conditions. This method was found to be very effective as a variety of terminal alkynes bearing aliphatic or aromatic substituents underwent smooth transformation to their corresponding silylated products in excellent yields within a few minutes using N-heterocyclic carbene as an organo-catalyst. This methodology was also applied to the chemospecific N-silylation of indoles.</abstract><doi>10.1039/C4RA08727E</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2014-01, Vol.4 (91), p.49775-49779 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1651378764 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Aliphatic compounds Alkynes Carbenes Indoles Solvents Terminals Transformations Trimethylsilylation |
| title | NHC catalysed trimethylsilylation of terminal alkynes and indoles with Ruppert's reagent under solvent free conditions |
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