Visible‐Light‐Mediated α‐Oxygenation of 3‐(N,N‐Dimethylaminomethyl)‐Indoles to Aldehydes
The visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents afforded a series of 3‐carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)‐vi...
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| Veröffentlicht in: | European journal of organic chemistry 2018-12, Vol.2018 (47), p.6624-6628 |
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| container_issue | 47 |
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| container_title | European journal of organic chemistry |
| container_volume | 2018 |
| creator | Stanek, Filip Pawłowski, Robert Mlynarski, Jacek Stodulski, Maciej |
| description | The visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents afforded a series of 3‐carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)‐vincorine is described as well.
3‐Carbaindole derivatives can be accessed through a visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents. A plausible mechanism and practical application of this transformation in formal synthesis of (–)‐Vincorine is also described. |
| doi_str_mv | 10.1002/ejoc.201801335 |
| format | Article |
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3‐Carbaindole derivatives can be accessed through a visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents. A plausible mechanism and practical application of this transformation in formal synthesis of (–)‐Vincorine is also described.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201801335</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aldehydes ; Brønsted acids ; Indole ; Indoles ; Oxygenation ; Photocatalysis ; Photoredox</subject><ispartof>European journal of organic chemistry, 2018-12, Vol.2018 (47), p.6624-6628</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3175-9765c38c106b37a804ccf208e70fcd58527da648ff312ef0122afaeb3f77e6103</citedby><cites>FETCH-LOGICAL-c3175-9765c38c106b37a804ccf208e70fcd58527da648ff312ef0122afaeb3f77e6103</cites><orcidid>0000-0002-1794-306X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201801335$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201801335$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Stanek, Filip</creatorcontrib><creatorcontrib>Pawłowski, Robert</creatorcontrib><creatorcontrib>Mlynarski, Jacek</creatorcontrib><creatorcontrib>Stodulski, Maciej</creatorcontrib><title>Visible‐Light‐Mediated α‐Oxygenation of 3‐(N,N‐Dimethylaminomethyl)‐Indoles to Aldehydes</title><title>European journal of organic chemistry</title><description>The visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents afforded a series of 3‐carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)‐vincorine is described as well.
3‐Carbaindole derivatives can be accessed through a visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents. A plausible mechanism and practical application of this transformation in formal synthesis of (–)‐Vincorine is also described.</description><subject>Aldehydes</subject><subject>Brønsted acids</subject><subject>Indole</subject><subject>Indoles</subject><subject>Oxygenation</subject><subject>Photocatalysis</subject><subject>Photoredox</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFUEFOwzAQjBBIlMKVcyQuIJGyjpPYOValQFFpL4C4WW6ybl2lcYlTQW48ga_wER7BS3AVBEdOMzua2ZHG844J9AhAeIFLk_VCIBwIpfGO1yGQpgEkKew6HtEoICl92vcOrF0CQJokpOPho7Z6VuDX2_tYzxe1wzvMtawx9z8_3DV9beZYylqb0jfKp046nZxPHFzqFdaLppArXZqWnjl5VOamQOvXxu8XOS6aHO2ht6dkYfHoB7vew9XwfnATjKfXo0F_HGSUsDhIWRJnlGcEkhllkkOUZSoEjgxUlsc8Dlkuk4grRUmICkgYSiVxRhVjmBCgXe-k_buuzPMGbS2WZlOVrlKEJOaEAWeRc_VaV1YZaytUYl3plawaQUBspxTbKcXvlC6QtoEXXWDzj1sMb6eDv-w3Py5-pQ</recordid><startdate>20181219</startdate><enddate>20181219</enddate><creator>Stanek, Filip</creator><creator>Pawłowski, Robert</creator><creator>Mlynarski, Jacek</creator><creator>Stodulski, Maciej</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-1794-306X</orcidid></search><sort><creationdate>20181219</creationdate><title>Visible‐Light‐Mediated α‐Oxygenation of 3‐(N,N‐Dimethylaminomethyl)‐Indoles to Aldehydes</title><author>Stanek, Filip ; Pawłowski, Robert ; Mlynarski, Jacek ; Stodulski, Maciej</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3175-9765c38c106b37a804ccf208e70fcd58527da648ff312ef0122afaeb3f77e6103</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Aldehydes</topic><topic>Brønsted acids</topic><topic>Indole</topic><topic>Indoles</topic><topic>Oxygenation</topic><topic>Photocatalysis</topic><topic>Photoredox</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Stanek, Filip</creatorcontrib><creatorcontrib>Pawłowski, Robert</creatorcontrib><creatorcontrib>Mlynarski, Jacek</creatorcontrib><creatorcontrib>Stodulski, Maciej</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Stanek, Filip</au><au>Pawłowski, Robert</au><au>Mlynarski, Jacek</au><au>Stodulski, Maciej</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible‐Light‐Mediated α‐Oxygenation of 3‐(N,N‐Dimethylaminomethyl)‐Indoles to Aldehydes</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-12-19</date><risdate>2018</risdate><volume>2018</volume><issue>47</issue><spage>6624</spage><epage>6628</epage><pages>6624-6628</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents afforded a series of 3‐carbaindole derivatives. Herein we describe the reaction scope, a plausible mechanism and a practical application of this transformation in the formal synthesis of (–)‐vincorine is described as well.
3‐Carbaindole derivatives can be accessed through a visible‐light‐mediated oxygenation of 3‐N,N‐(dimethylaminomethyl)‐indoles bearing various substituents. A plausible mechanism and practical application of this transformation in formal synthesis of (–)‐Vincorine is also described.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201801335</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-1794-306X</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Aldehydes Brønsted acids Indole Indoles Oxygenation Photocatalysis Photoredox |
| title | Visible‐Light‐Mediated α‐Oxygenation of 3‐(N,N‐Dimethylaminomethyl)‐Indoles to Aldehydes |
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