Indium-Catalyzed Reductive Alkylation of Pyrroles with Alkynes and Hydrosilanes: Selective Synthesis of β-Alkylpyrroles
Mixing readily available alkynes, pyrroles, and triethylsilane along with an indium catalyst was found to be an efficient procedure to introduce alkyl groups onto a β-position of pyrroles in a complete regioselective manner. This is the first demonstration of catalytic β-alkylation of pyrroles in a...
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| Veröffentlicht in: | Organic letters 2009-05, Vol.11 (10), p.2129-2132 |
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| container_end_page | 2132 |
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| container_issue | 10 |
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| container_title | Organic letters |
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| creator | Tsuchimoto, Teruhisa Wagatsuma, Tatsuya Aoki, Kazuki Shimotori, Jun |
| description | Mixing readily available alkynes, pyrroles, and triethylsilane along with an indium catalyst was found to be an efficient procedure to introduce alkyl groups onto a β-position of pyrroles in a complete regioselective manner. This is the first demonstration of catalytic β-alkylation of pyrroles in a single step. |
| doi_str_mv | 10.1021/ol900651u |
| format | Article |
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Lett</addtitle><description>Mixing readily available alkynes, pyrroles, and triethylsilane along with an indium catalyst was found to be an efficient procedure to introduce alkyl groups onto a β-position of pyrroles in a complete regioselective manner. This is the first demonstration of catalytic β-alkylation of pyrroles in a single step.</description><subject>Alkylation</subject><subject>Alkynes - chemistry</subject><subject>Catalysis</subject><subject>Indium - chemistry</subject><subject>Molecular Structure</subject><subject>Pyrroles - chemical synthesis</subject><subject>Pyrroles - chemistry</subject><subject>Silanes - chemistry</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkEFOwzAQRS0EoqWw4AIoG5BYBGyncWJ2VQW0UiUQhXXk2mM1xYlLnADhWByEM5E2Udmwsj1-8zTzETol-IpgSq6t4RizkFR7qE9CGvgRDun-7s5wDx05t8KYNBV-iHqEBzGNWNxHn9NcpVXmj0UpTP0FynsCVckyfQdvZF5rI8rU5p7V3mNdFNaA8z7Scrn9y5uHyJU3qVVhXWpEU7jx5mCg7Z_XebkEl7pN-8-3v_WtO80xOtDCODjpzgF6ubt9Hk_82cP9dDya-SIgQenHmEnGYgZ0wQVwokkAdBhHWoSh5JTwKOSM0KGgWirJAkziIUQ01CxSWIEOBuii9a4L-1aBK5MsdRLMZlpbuYRFFHMWsga8bEHZLOMK0Mm6SDNR1AnBySbmZBdzw5510mqRgfoju1wb4LwFhHTJylZF3uz4j-gXQAuGhw</recordid><startdate>20090521</startdate><enddate>20090521</enddate><creator>Tsuchimoto, Teruhisa</creator><creator>Wagatsuma, Tatsuya</creator><creator>Aoki, Kazuki</creator><creator>Shimotori, Jun</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>20090521</creationdate><title>Indium-Catalyzed Reductive Alkylation of Pyrroles with Alkynes and Hydrosilanes: Selective Synthesis of β-Alkylpyrroles</title><author>Tsuchimoto, Teruhisa ; Wagatsuma, Tatsuya ; Aoki, Kazuki ; Shimotori, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-806c6686e2b9ae91f13e2487fa55c92197596124a2fcdc630184e725f67d0def3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Alkylation</topic><topic>Alkynes - chemistry</topic><topic>Catalysis</topic><topic>Indium - chemistry</topic><topic>Molecular Structure</topic><topic>Pyrroles - chemical synthesis</topic><topic>Pyrroles - chemistry</topic><topic>Silanes - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tsuchimoto, Teruhisa</creatorcontrib><creatorcontrib>Wagatsuma, Tatsuya</creatorcontrib><creatorcontrib>Aoki, Kazuki</creatorcontrib><creatorcontrib>Shimotori, Jun</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>Tsuchimoto, Teruhisa</au><au>Wagatsuma, Tatsuya</au><au>Aoki, Kazuki</au><au>Shimotori, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Indium-Catalyzed Reductive Alkylation of Pyrroles with Alkynes and Hydrosilanes: Selective Synthesis of β-Alkylpyrroles</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2009-05, Vol.11 (10), p.2129-2132 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_67209656 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkylation Alkynes - chemistry Catalysis Indium - chemistry Molecular Structure Pyrroles - chemical synthesis Pyrroles - chemistry Silanes - chemistry Stereoisomerism |
| title | Indium-Catalyzed Reductive Alkylation of Pyrroles with Alkynes and Hydrosilanes: Selective Synthesis of β-Alkylpyrroles |
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