Brønsted Acid Catalyzed α′-Functionalization of Silylenol Ethers with Indoles
A new method which enables carbon–carbon bond formation at the α′‐position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole‐containing silylenol ethers in excellent yields with...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2015-04, Vol.54 (15), p.4641-4645 |
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| container_end_page | 4645 |
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| container_issue | 15 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Ayala, Caitlan E. Dange, Nitin S. Fronczek, Frank R. Kartika, Rendy |
| description | A new method which enables carbon–carbon bond formation at the α′‐position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole‐containing silylenol ethers in excellent yields with complete regiocontrol, presumably through silyloxyallyl cation intermediates. Despite the use of Brønsted acid, the silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.
Under control: The title reaction enables CC bond formation at the α′‐position of silylenol ethers. Highly substituted indole‐containing silylenol ethers are generated in excellent yields with complete regiocontrol presumably through silyloxyallyl cation intermediates. The silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions. |
| doi_str_mv | 10.1002/anie.201409758 |
| format | Article |
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Under control: The title reaction enables CC bond formation at the α′‐position of silylenol ethers. Highly substituted indole‐containing silylenol ethers are generated in excellent yields with complete regiocontrol presumably through silyloxyallyl cation intermediates. The silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201409758</identifier><identifier>PMID: 25694101</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Brønsted acid ; heterocycles ; nucleophilic substitution ; oxyallyl cations ; silylenol ethers</subject><ispartof>Angewandte Chemie International Edition, 2015-04, Vol.54 (15), p.4641-4645</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5238-2704a9df096671bb4e391fdeef607dfa120b9710f93762d68710c13e769053af3</citedby><cites>FETCH-LOGICAL-c5238-2704a9df096671bb4e391fdeef607dfa120b9710f93762d68710c13e769053af3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201409758$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201409758$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25694101$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ayala, Caitlan E.</creatorcontrib><creatorcontrib>Dange, Nitin S.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Kartika, Rendy</creatorcontrib><title>Brønsted Acid Catalyzed α′-Functionalization of Silylenol Ethers with Indoles</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A new method which enables carbon–carbon bond formation at the α′‐position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole‐containing silylenol ethers in excellent yields with complete regiocontrol, presumably through silyloxyallyl cation intermediates. Despite the use of Brønsted acid, the silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.
Under control: The title reaction enables CC bond formation at the α′‐position of silylenol ethers. Highly substituted indole‐containing silylenol ethers are generated in excellent yields with complete regiocontrol presumably through silyloxyallyl cation intermediates. The silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.</description><subject>Brønsted acid</subject><subject>heterocycles</subject><subject>nucleophilic substitution</subject><subject>oxyallyl cations</subject><subject>silylenol ethers</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkLFOwzAURS0EoqWwMqKMLCl2nNjxWKq2FJUiBAiJxXITWzW4CcSJSjvxSzCxs_MRfAmuUio2Jl9L517pHQAOEWwjCIMTkWnZDiAKIaNRvAWaKAqQjynF2y6HGPs0jlAD7Fn74Pg4hmQXNIKIsBBB1ARXp8XnR2ZLmXqdRKdeV5TCLJbu-_X2_fru96ssKXWeCaOXYhW8XHnX2iyMzHLj9cqpLKw31-XUG2ZpbqTdBztKGCsP1m8L3PZ7N90zf3Q5GHY7Iz-JAhz7AYWhYKmCjBCKJpNQYoZUKqUikKZKoABOGEVQMUxJkJLY5QRhSQmDERYKt8BxvftU5M-VtCWfaZtIY0Qm88pyRNyNYcwIdmi7RpMit7aQij8VeiaKBUeQrzTylUa-0egKR-vtajKT6Qb_9eYAVgNzbeTinzneGQ97f8f9uqud9pdNVxSPnFBMI343HnA2IiM4OL_nF_gHlbqP1w</recordid><startdate>20150407</startdate><enddate>20150407</enddate><creator>Ayala, Caitlan E.</creator><creator>Dange, Nitin S.</creator><creator>Fronczek, Frank R.</creator><creator>Kartika, Rendy</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150407</creationdate><title>Brønsted Acid Catalyzed α′-Functionalization of Silylenol Ethers with Indoles</title><author>Ayala, Caitlan E. ; Dange, Nitin S. ; Fronczek, Frank R. ; Kartika, Rendy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5238-2704a9df096671bb4e391fdeef607dfa120b9710f93762d68710c13e769053af3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Brønsted acid</topic><topic>heterocycles</topic><topic>nucleophilic substitution</topic><topic>oxyallyl cations</topic><topic>silylenol ethers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ayala, Caitlan E.</creatorcontrib><creatorcontrib>Dange, Nitin S.</creatorcontrib><creatorcontrib>Fronczek, Frank R.</creatorcontrib><creatorcontrib>Kartika, Rendy</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ayala, Caitlan E.</au><au>Dange, Nitin S.</au><au>Fronczek, Frank R.</au><au>Kartika, Rendy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Brønsted Acid Catalyzed α′-Functionalization of Silylenol Ethers with Indoles</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2015-04-07</date><risdate>2015</risdate><volume>54</volume><issue>15</issue><spage>4641</spage><epage>4645</epage><pages>4641-4645</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>A new method which enables carbon–carbon bond formation at the α′‐position of silylenol ethers by using catalytic amounts of pyridinium triflate is reported. This chemistry successfully produces, structurally challenging, highly substituted indole‐containing silylenol ethers in excellent yields with complete regiocontrol, presumably through silyloxyallyl cation intermediates. Despite the use of Brønsted acid, the silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.
Under control: The title reaction enables CC bond formation at the α′‐position of silylenol ethers. Highly substituted indole‐containing silylenol ethers are generated in excellent yields with complete regiocontrol presumably through silyloxyallyl cation intermediates. The silylenol ether moiety does not undergo protodesilylation, thus underscoring the very mild reaction conditions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>25694101</pmid><doi>10.1002/anie.201409758</doi><tpages>5</tpages></addata></record> |
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| source | Access via Wiley Online Library |
| subjects | Brønsted acid heterocycles nucleophilic substitution oxyallyl cations silylenol ethers |
| title | Brønsted Acid Catalyzed α′-Functionalization of Silylenol Ethers with Indoles |
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