Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents
Direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions by using sodium trifluoromethanesulfinate were promoted by different phosphorus reagents to selectively occur under mild and transition‐metal‐free conditions. In the presence of phosphorus trichloride, sodium trifluoromethan...
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| Veröffentlicht in: | European journal of organic chemistry 2017-06, Vol.2017 (24), p.3505-3511 |
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| container_issue | 24 |
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| container_title | European journal of organic chemistry |
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| creator | Sun, Dong‐Wei Jiang, Xu Jiang, Min Lin, Yun Liu, Jin‐Tao |
| description | Direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions by using sodium trifluoromethanesulfinate were promoted by different phosphorus reagents to selectively occur under mild and transition‐metal‐free conditions. In the presence of phosphorus trichloride, sodium trifluoromethanesulfinate readily underwent a reaction with indole and its derivatives in N,N‐dimethylformamide (DMF) at room temperature to give 3‐trifluoromethylthiolated products in good yields. Trifluoromethylsulfinylation reactions, however, occurred at the C‐3 position when phosphorus oxychloride was used to give the corresponding sulfoxides in high yields. This protocol was further extended to the use of other sodium perfluoroalkanesulfinates.
A facile method for the selective trifluoromethylthiolation and trifluoromethylsulfinylation of indoles was developed. Sodium trifluoromethanesulfinate was used in the preparation of a series of trifluoromethylthio‐ and trifluoromethylsulfinyl‐containing compounds in good yields under mild and transition‐metal‐free conditions. |
| doi_str_mv | 10.1002/ejoc.201700661 |
| format | Article |
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A facile method for the selective trifluoromethylthiolation and trifluoromethylsulfinylation of indoles was developed. Sodium trifluoromethanesulfinate was used in the preparation of a series of trifluoromethylthio‐ and trifluoromethylsulfinyl‐containing compounds in good yields under mild and transition‐metal‐free conditions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201700661</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Derivatives ; Fluorinated compounds ; Fluorine ; Indoles ; Nitrogen heterocycles ; Phosphorus ; Reagents ; Sodium ; Sulfinates ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2017-06, Vol.2017 (24), p.3505-3511</ispartof><rights>2017 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3171-ad3d6473acf8921ee17b823bc4c16840395f0e05addc1d5853f60e8fd5fabf853</citedby><cites>FETCH-LOGICAL-c3171-ad3d6473acf8921ee17b823bc4c16840395f0e05addc1d5853f60e8fd5fabf853</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%2Fejoc.201700661$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201700661$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Sun, Dong‐Wei</creatorcontrib><creatorcontrib>Jiang, Xu</creatorcontrib><creatorcontrib>Jiang, Min</creatorcontrib><creatorcontrib>Lin, Yun</creatorcontrib><creatorcontrib>Liu, Jin‐Tao</creatorcontrib><title>Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents</title><title>European journal of organic chemistry</title><description>Direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions by using sodium trifluoromethanesulfinate were promoted by different phosphorus reagents to selectively occur under mild and transition‐metal‐free conditions. In the presence of phosphorus trichloride, sodium trifluoromethanesulfinate readily underwent a reaction with indole and its derivatives in N,N‐dimethylformamide (DMF) at room temperature to give 3‐trifluoromethylthiolated products in good yields. Trifluoromethylsulfinylation reactions, however, occurred at the C‐3 position when phosphorus oxychloride was used to give the corresponding sulfoxides in high yields. This protocol was further extended to the use of other sodium perfluoroalkanesulfinates.
A facile method for the selective trifluoromethylthiolation and trifluoromethylsulfinylation of indoles was developed. Sodium trifluoromethanesulfinate was used in the preparation of a series of trifluoromethylthio‐ and trifluoromethylsulfinyl‐containing compounds in good yields under mild and transition‐metal‐free conditions.</description><subject>Derivatives</subject><subject>Fluorinated compounds</subject><subject>Fluorine</subject><subject>Indoles</subject><subject>Nitrogen heterocycles</subject><subject>Phosphorus</subject><subject>Reagents</subject><subject>Sodium</subject><subject>Sulfinates</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LAzEQhhdRsFavngOet066nzlKqVoptNgK3pbsZuKmbDc1yVr2h_h_3bJF0YunmUmeZwZez7umMKIA41vc6GI0BpoAxDE98QYUGPMhZnDa9WEQ-pQFr-fehbUbAGAdNPA-V1hh4dQHkrVRsmq00Vt0ZVu5UumKO6Vrwmvx99c2lVR1ewS0JLNa6Aot2StXkpUWqtn-dniNvcQdkmX3ph0KkrdkWWq7K7VpLHlG_oa1s5femeSVxatjHXov99P15NGfLx5mk7u5XwQ0oT4XgYjDJOCFTNmYItIkT8dBXoQFjdMQAhZJQIi4EAUVURoFMgZMpYgkz2U3Dr2bfu_O6PcGrcs2ujF1dzKjjIYJi2KadtSopwqjrTUos51RW27ajEJ2iD47RJ99R98JrBf2qsL2HzqbPi0mP-4Xea6Okw</recordid><startdate>20170630</startdate><enddate>20170630</enddate><creator>Sun, Dong‐Wei</creator><creator>Jiang, Xu</creator><creator>Jiang, Min</creator><creator>Lin, Yun</creator><creator>Liu, Jin‐Tao</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20170630</creationdate><title>Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents</title><author>Sun, Dong‐Wei ; Jiang, Xu ; Jiang, Min ; Lin, Yun ; Liu, Jin‐Tao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3171-ad3d6473acf8921ee17b823bc4c16840395f0e05addc1d5853f60e8fd5fabf853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Derivatives</topic><topic>Fluorinated compounds</topic><topic>Fluorine</topic><topic>Indoles</topic><topic>Nitrogen heterocycles</topic><topic>Phosphorus</topic><topic>Reagents</topic><topic>Sodium</topic><topic>Sulfinates</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Dong‐Wei</creatorcontrib><creatorcontrib>Jiang, Xu</creatorcontrib><creatorcontrib>Jiang, Min</creatorcontrib><creatorcontrib>Lin, Yun</creatorcontrib><creatorcontrib>Liu, Jin‐Tao</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sun, Dong‐Wei</au><au>Jiang, Xu</au><au>Jiang, Min</au><au>Lin, Yun</au><au>Liu, Jin‐Tao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents</atitle><jtitle>European journal of organic chemistry</jtitle><date>2017-06-30</date><risdate>2017</risdate><volume>2017</volume><issue>24</issue><spage>3505</spage><epage>3511</epage><pages>3505-3511</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Direct trifluoromethylthiolation and trifluoromethylsulfinylation reactions by using sodium trifluoromethanesulfinate were promoted by different phosphorus reagents to selectively occur under mild and transition‐metal‐free conditions. In the presence of phosphorus trichloride, sodium trifluoromethanesulfinate readily underwent a reaction with indole and its derivatives in N,N‐dimethylformamide (DMF) at room temperature to give 3‐trifluoromethylthiolated products in good yields. Trifluoromethylsulfinylation reactions, however, occurred at the C‐3 position when phosphorus oxychloride was used to give the corresponding sulfoxides in high yields. This protocol was further extended to the use of other sodium perfluoroalkanesulfinates.
A facile method for the selective trifluoromethylthiolation and trifluoromethylsulfinylation of indoles was developed. Sodium trifluoromethanesulfinate was used in the preparation of a series of trifluoromethylthio‐ and trifluoromethylsulfinyl‐containing compounds in good yields under mild and transition‐metal‐free conditions.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201700661</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Derivatives Fluorinated compounds Fluorine Indoles Nitrogen heterocycles Phosphorus Reagents Sodium Sulfinates Synthetic methods |
| title | Selective Trifluoromethylthiolation and Trifluoromethylsulfinylation of Indoles with Sodium Trifluoromethanesulfinate Promoted by Phosphorus Reagents |
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