SO2ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles
A direct and one-step method for the synthesis of 3-chloro-2-formylindoles with SO2ClF is reported. This tandem system consists of double electrophilic chlorination and deprotonation, nucleophilic addition of H2O to the resulting enamine intermediate, and subsequent oxidation. Various readily availa...
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| Veröffentlicht in: | Organic chemistry frontiers an international journal of organic chemistry 2023-08, Vol.10 (16), p.4100-4104 |
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| container_issue | 16 |
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| container_title | Organic chemistry frontiers an international journal of organic chemistry |
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| creator | Zheng, Yu Ma, Tianting Liu, Bingcong Huang, Shenlin |
| description | A direct and one-step method for the synthesis of 3-chloro-2-formylindoles with SO2ClF is reported. This tandem system consists of double electrophilic chlorination and deprotonation, nucleophilic addition of H2O to the resulting enamine intermediate, and subsequent oxidation. Various readily available 2-methylindoles were applicable to this protocol under mild conditions, furnishing 2,3-difunctionalized indoles in good to high yields. |
| doi_str_mv | 10.1039/d3qo00879g |
| format | Article |
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This tandem system consists of double electrophilic chlorination and deprotonation, nucleophilic addition of H2O to the resulting enamine intermediate, and subsequent oxidation. Various readily available 2-methylindoles were applicable to this protocol under mild conditions, furnishing 2,3-difunctionalized indoles in good to high yields.</description><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/d3qo00879g</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Chlorination ; Indoles ; Organic chemistry ; Oxidation</subject><ispartof>Organic chemistry frontiers an international journal of organic chemistry, 2023-08, Vol.10 (16), p.4100-4104</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Zheng, Yu</creatorcontrib><creatorcontrib>Ma, Tianting</creatorcontrib><creatorcontrib>Liu, Bingcong</creatorcontrib><creatorcontrib>Huang, Shenlin</creatorcontrib><title>SO2ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles</title><title>Organic chemistry frontiers an international journal of organic chemistry</title><description>A direct and one-step method for the synthesis of 3-chloro-2-formylindoles with SO2ClF is reported. This tandem system consists of double electrophilic chlorination and deprotonation, nucleophilic addition of H2O to the resulting enamine intermediate, and subsequent oxidation. Various readily available 2-methylindoles were applicable to this protocol under mild conditions, furnishing 2,3-difunctionalized indoles in good to high yields.</description><subject>Chlorination</subject><subject>Indoles</subject><subject>Organic chemistry</subject><subject>Oxidation</subject><issn>2052-4110</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpNj09LAzEUxIMoWGovfoKAV6Mv_za73qTYKhR6UM8lm5e1KdtN26RgBb-7W-3Bubw5DL83Q8g1hzsOsrpHuY0Apak-zshAgBZMcQ7n__wlGaW0AgAudAHaDMj361yM2wnb7OI6Zo_ULdu4C53NIXYsfgb8dTQ2VLC1z8tDGzqMrU8P1NLYeZay39B06PLS5-DoMROR5kitcz4lKm4lw9DsO3cE2TZ89V9OjCty0dg2-dHpDsn75Olt_Mxm8-nL-HHGNryUmRmsatN3Vhw0il4ojFbaIjTW1L5wqhLOKfSoPNQodKV5WWrglVPalYUckps_bj9zu_cpL1Zxv-vLpIUolREFl9zIH2wFYRY</recordid><startdate>20230808</startdate><enddate>20230808</enddate><creator>Zheng, Yu</creator><creator>Ma, Tianting</creator><creator>Liu, Bingcong</creator><creator>Huang, Shenlin</creator><general>Royal Society of Chemistry</general><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope></search><sort><creationdate>20230808</creationdate><title>SO2ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles</title><author>Zheng, Yu ; Ma, Tianting ; Liu, Bingcong ; Huang, Shenlin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p183t-7d9b70124105d2222d27545ad0fa7be6c492cc4ded4e0bd25951885019c45c863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Chlorination</topic><topic>Indoles</topic><topic>Organic chemistry</topic><topic>Oxidation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zheng, Yu</creatorcontrib><creatorcontrib>Ma, Tianting</creatorcontrib><creatorcontrib>Liu, Bingcong</creatorcontrib><creatorcontrib>Huang, Shenlin</creatorcontrib><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zheng, Yu</au><au>Ma, Tianting</au><au>Liu, Bingcong</au><au>Huang, Shenlin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>SO2ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles</atitle><jtitle>Organic chemistry frontiers an international journal of organic chemistry</jtitle><date>2023-08-08</date><risdate>2023</risdate><volume>10</volume><issue>16</issue><spage>4100</spage><epage>4104</epage><pages>4100-4104</pages><issn>2052-4110</issn><eissn>2052-4110</eissn><abstract>A direct and one-step method for the synthesis of 3-chloro-2-formylindoles with SO2ClF is reported. This tandem system consists of double electrophilic chlorination and deprotonation, nucleophilic addition of H2O to the resulting enamine intermediate, and subsequent oxidation. Various readily available 2-methylindoles were applicable to this protocol under mild conditions, furnishing 2,3-difunctionalized indoles in good to high yields.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d3qo00879g</doi><tpages>5</tpages></addata></record> |
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| ispartof | Organic chemistry frontiers an international journal of organic chemistry, 2023-08, Vol.10 (16), p.4100-4104 |
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| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Chlorination Indoles Organic chemistry Oxidation |
| title | SO2ClF-promoted chlorination-oxidation of 2-methylindoles: a one-step synthetic method to access 2,3-difunctionalized indoles |
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