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Synthesis 2017; 49(21): 4827-4844
DOI: 10.1055/s-0036-1589514
DOI: 10.1055/s-0036-1589514
feature
A Radical Access to CF3- and SF5-Containing Dihydrobenzofurans and Indolines
This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC), the Fonds de recherche du Québec – Nature et technologies (FRQNT), the FRQNT Centre in Green Chemistry and Catalysis (CCVC), and the Université Laval.Further Information
Publication History
Received: 29 August 2017
Accepted: 05 September 2017
Publication Date:
04 October 2017 (online)
‡ These authors contributed equally to this work.
Abstract
The synthesis of 3-(2,2,2-trifluoroethyl)-2,3-dihydrobenzofurans, 3-(2,2,2-trifluoroethyl)indolines, 3-[(pentafluorosulfanyl)methyl]-2,3-dihydrobenzofurans, and 3-[(pentafluorosulfanyl)methyl]indolines using an intramolecular reductive radical cyclization from readily available acyclic precursors is reported. The CF3- and SF5-containing heterocycles are obtained in moderate to excellent yields. Notably, this transformation represents the first example of an aryl radical addition to a SF5-containing alkene. Finally, the possibility of oxidation of some of the products generated to benzofurans and indoles is shown.
Key words
heterocycles - fluorine - radical reaction - pentafluorosulfanyl - trifluoromethyl - dihydrobenzofurans - indolinesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0035-1589514.
- Supporting Information
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A similar process was used for a radical clock experiment, see:
For selected examples of bioactive 3-(2,2,2-trifluoroethyl)-2,3-dihydrobenzofuran and 3-(2,2,2-trifluoroethyl)indoline derivatives, see:
Reviews:
For selected examples, see:
For selected examples, see:
For selected examples, see:
Pentafluoro(3-hydroxy-1-propenyl)sulfur (7) is commercially available, but it can also be prepared from allyl alcohol or allyl acetate using SF5Cl, see:
For instance, see:
For example, see: