Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions

Indoles, when treated with dimethyl diazomalonate under catalysis by Cu(acac)2, undergo C−H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. Indoles where the 3-position is substituted give high yields of the C2−H insertion product. Microwave condition...

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Veröffentlicht in:	Organic letters 2010-11, Vol.12 (21), p.4956-4959
Hauptverfasser:	Johansen, Michael B, Kerr, Michael A
Format:	Artikel
Sprache:	eng
Schlagworte:	Catalysis Copper - chemistry Indoles - chemistry Methane - analogs & derivatives Methane - chemistry Molecular Structure
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description	Indoles, when treated with dimethyl diazomalonate under catalysis by Cu(acac)2, undergo C−H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. Indoles where the 3-position is substituted give high yields of the C2−H insertion product. Microwave conditions are also disclosed which show comparable yields with reduced reaction times.
doi_str_mv	10.1021/ol1020948
format	Article
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Lett</addtitle><description>Indoles, when treated with dimethyl diazomalonate under catalysis by Cu(acac)2, undergo C−H insertion reactions regioselectively depending on the substitution pattern on the indole moiety. Indoles where the 3-position is substituted give high yields of the C2−H insertion product. Microwave conditions are also disclosed which show comparable yields with reduced reaction times.</description><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Indoles - chemistry</subject><subject>Methane - analogs & derivatives</subject><subject>Methane - chemistry</subject><subject>Molecular Structure</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkDtPwzAUhS0EoqUw8AdQFoQYAnac-MGGwqtSERKCObr1Q0rlxsVOhvbX46qlE9M5uvruGT6ELgm-I7gg996lwLIUR2hMqoLmHFfF8aEzPEJnMS4wJukiT9EowZSJSozR51MbjOqzl6FTfes7cO0GtiXzNpt22jsTH7Lar1Ym5DX04NYbo7N3cL5bu6yGMDedb3Viownbx3iOTiy4aC72OUHfL89f9Vs--3id1o-zHKjAfa4U17ycy4KDliUFsFwwLajWJRUFsdwqgwtBCNNKCllWsmKccVtZYNTYik7QzW53FfzPYGLfLNuojHPQGT_EhrOi5JJwnsjbHamCjzEY26xCu4Swbghutgabg8HEXu1Xh_nS6AP5pywB1zsAVGwWfgjJWfxn6Bdc6nct</recordid><startdate>20101105</startdate><enddate>20101105</enddate><creator>Johansen, Michael B</creator><creator>Kerr, Michael A</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>20101105</creationdate><title>Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions</title><author>Johansen, Michael B ; Kerr, Michael A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-cc7d74b927ad943aaf786d83dd43821f7fce028116dc98945956767f5fa63ef53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Indoles - chemistry</topic><topic>Methane - analogs & derivatives</topic><topic>Methane - chemistry</topic><topic>Molecular Structure</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Johansen, Michael B</creatorcontrib><creatorcontrib>Kerr, Michael 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>Johansen, Michael B</au><au>Kerr, Michael A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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subjects	Catalysis Copper - chemistry Indoles - chemistry Methane - analogs & derivatives Methane - chemistry Molecular Structure
title	Direct Functionalization of Indoles: Copper-Catalyzed Malonyl Carbenoid Insertions
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