Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives
Abstract A photocatalyzed and highly efficient trifluoromethylation of N -arylvinylsulfonamides using commercially available CF 3 SO 2 Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of th...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2022-02, Vol.54 (3), p.667-682 |
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| container_start_page | 667 |
| container_title | Synthesis (Stuttgart) |
| container_volume | 54 |
| creator | Vytla, Devaiah Kaliyaperumal, Kumargurubaran Velayuthaperumal, Rajeswari Shaw, Parinita Gautam, Raj Mathur, Arvind Roy, Amrita |
| description | Abstract
A photocatalyzed and highly efficient trifluoromethylation of
N
-arylvinylsulfonamides using commercially available CF
3
SO
2
Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in good to excellent yields. |
| doi_str_mv | 10.1055/s-0040-1720921 |
| format | Article |
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A photocatalyzed and highly efficient trifluoromethylation of
N
-arylvinylsulfonamides using commercially available CF
3
SO
2
Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in good to excellent yields.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0040-1720921</identifier><language>eng</language><publisher>Rüdigerstraße 14, 70469 Stuttgart, Germany: Georg Thieme Verlag KG</publisher><ispartof>Synthesis (Stuttgart), 2022-02, Vol.54 (3), p.667-682</ispartof><rights>Thieme. All rights reserved</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c207t-2557415c73bc641fc2177dd21377dc9aba8143fafbc07b774b99669959d2121a3</citedby><cites>FETCH-LOGICAL-c207t-2557415c73bc641fc2177dd21377dc9aba8143fafbc07b774b99669959d2121a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1720921.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0040-1720921$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,776,780,3004,3005,27901,27902,54534,54535</link.rule.ids></links><search><creatorcontrib>Vytla, Devaiah</creatorcontrib><creatorcontrib>Kaliyaperumal, Kumargurubaran</creatorcontrib><creatorcontrib>Velayuthaperumal, Rajeswari</creatorcontrib><creatorcontrib>Shaw, Parinita</creatorcontrib><creatorcontrib>Gautam, Raj</creatorcontrib><creatorcontrib>Mathur, Arvind</creatorcontrib><creatorcontrib>Roy, Amrita</creatorcontrib><title>Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
A photocatalyzed and highly efficient trifluoromethylation of
N
-arylvinylsulfonamides using commercially available CF
3
SO
2
Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[
c
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A photocatalyzed and highly efficient trifluoromethylation of
N
-arylvinylsulfonamides using commercially available CF
3
SO
2
Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild conditions. An investigation of the substrate scope is performed to establish a general, synthetically useful protocol for the synthesis of novel trifluoromethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in moderate to high yields. This method is also successfully applied for the synthesis of difluoromethylated and trifluoroethylated 1,3-dihydrobenzo[
c
]isothiazole 2,2-dioxides in good to excellent yields.</abstract><cop>Rüdigerstraße 14, 70469 Stuttgart, Germany</cop><pub>Georg Thieme Verlag KG</pub><doi>10.1055/s-0040-1720921</doi><tpages>16</tpages></addata></record> |
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| ispartof | Synthesis (Stuttgart), 2022-02, Vol.54 (3), p.667-682 |
| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0040_1720921 |
| source | Thieme - Connect here FIRST to enable access |
| title | Visible-Light-Promoted Radical Cyclization of N-Arylvinylsulfonamides: Synthesis of CF3/CHF2/CH2CF3-Containing 1,3-Dihydrobenzo[c]isothiazole 2,2-Dioxide Derivatives |
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