General and Efficient Synthesis of Indoles through Triazene-Directed C-H Annulation
Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl–alkyl and alkyl–alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring‐contraction‐triggered NN bond cleavage. I...
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Veröffentlicht in: | Angewandte Chemie International Edition 2013-05, Vol.52 (22), p.5795-5798 |
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description | Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl–alkyl and alkyl–alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring‐contraction‐triggered NN bond cleavage. It allows rapid conversion of the reaction products into several functional molecules. |
doi_str_mv | 10.1002/anie.201301742 |
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Excellent regioselectivity was accomplished for aryl–alkyl and alkyl–alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring‐contraction‐triggered NN bond cleavage. It allows rapid conversion of the reaction products into several functional molecules.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201301742</identifier><identifier>PMID: 23606211</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkynes ; Bonding ; Catalysis ; Chemical reactions ; Cleavage ; Conversion ; CH activation ; indole ; Indoles ; Indoles - chemical synthesis ; Migration ; Molecular Structure ; NN cleavage ; Rhodium ; Transition Elements - chemistry ; triazene ; Triazines - chemistry</subject><ispartof>Angewandte Chemie International Edition, 2013-05, Vol.52 (22), p.5795-5798</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. 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Chem. Int. Ed</addtitle><description>Unprotected indoles are prepared with the title method, which has a wide scope for alkynes. Excellent regioselectivity was accomplished for aryl–alkyl and alkyl–alkyl disubstituted acetylenes. This reaction features an unusual 1,2 rhodium migration and ring‐contraction‐triggered NN bond cleavage. It allows rapid conversion of the reaction products into several functional molecules.</description><subject>Alkynes</subject><subject>Bonding</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Cleavage</subject><subject>Conversion</subject><subject>CH activation</subject><subject>indole</subject><subject>Indoles</subject><subject>Indoles - chemical synthesis</subject><subject>Migration</subject><subject>Molecular Structure</subject><subject>NN cleavage</subject><subject>Rhodium</subject><subject>Transition Elements - chemistry</subject><subject>triazene</subject><subject>Triazines - chemistry</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqN0c1v0zAYBnALMbGxceWILHHhkmL7dezkWLrSFU2b0D7gZrnJa-qROsNOtHV__VJ1qyYucLIPv-eRXj2EvOdsxBkTn23wOBKMA-NailfkgOeCZ6A1vB7-EiDTRc73yduUbgZfFEy9IfsCFFOC8wNyMcOA0TbUhppOnfOVx9DRi3Xolph8oq2j81C3DSbaLWPb_1rSy-jtwxDLjn3EqsOaTrITOg6hb2zn23BE9pxtEr57eg_J1dfp5eQkOz2fzSfj06zKCy0yXmmsFZZSqLosFWMAWCplhXTAa6ldXijFRS14oZgr7HAigFgsHGAuBVdwSD5te29j-6fH1JmVTxU2jQ3Y9slwzTiT8F8UcpBas2JDP_5Fb9o-huGQjRLAtNByUKOtqmKbUkRnbqNf2bg2nJnNMmazjNktMwQ-PNX2ixXWO_48xQDKLbjzDa7_UWfGZ_Ppy_Jsm_Wpw_td1sbfRmnQuflxNjPy57frL_L7tTmGR8FDpeo</recordid><startdate>20130527</startdate><enddate>20130527</enddate><creator>Wang, Chengming</creator><creator>Sun, Huan</creator><creator>Fang, Yan</creator><creator>Huang, Yong</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><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>7TM</scope><scope>K9.</scope><scope>7X8</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20130527</creationdate><title>General and Efficient Synthesis of Indoles through Triazene-Directed C-H Annulation</title><author>Wang, Chengming ; Sun, Huan ; Fang, Yan ; Huang, Yong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5872-1c7ed6e9426d9960033e966a24f31d47f586612d21860f8a301332bbf3e542163</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkynes</topic><topic>Bonding</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Cleavage</topic><topic>Conversion</topic><topic>CH activation</topic><topic>indole</topic><topic>Indoles</topic><topic>Indoles - chemical synthesis</topic><topic>Migration</topic><topic>Molecular Structure</topic><topic>NN cleavage</topic><topic>Rhodium</topic><topic>Transition Elements - chemistry</topic><topic>triazene</topic><topic>Triazines - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Chengming</creatorcontrib><creatorcontrib>Sun, Huan</creatorcontrib><creatorcontrib>Fang, Yan</creatorcontrib><creatorcontrib>Huang, Yong</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Chengming</au><au>Sun, Huan</au><au>Fang, Yan</au><au>Huang, Yong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>General and Efficient Synthesis of Indoles through Triazene-Directed C-H Annulation</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. 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subjects | Alkynes Bonding Catalysis Chemical reactions Cleavage Conversion CH activation indole Indoles Indoles - chemical synthesis Migration Molecular Structure NN cleavage Rhodium Transition Elements - chemistry triazene Triazines - chemistry |
title | General and Efficient Synthesis of Indoles through Triazene-Directed C-H Annulation |
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