Complementary Methods for the Introduction of the (<i>E</i>)‐3‐(Pentafluorosulfanyl)allyl Chain unto O‐, N‐, S‐, and C‐Based Nucleophiles

Desroches, Justine; Forcellini, Elsa; Paquin, Jean‐François

doi:10.1002/ejoc.201600684

Cited by 9 publications

(5 citation statements)

References 42 publications

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“…[91] In 2016, the group of Paquin investigated two strategies using SF 5 -allylic alcohol 126 a as starting building block to attach the E-3-(pentafluorosulfanyl)allyl chain onto various nucleophiles. [92] One strategy was using the palladium-catalysed Tsuji-Trost coupling between allyl carbonate 128 and the desired nucleophiles, which was especially effective for phenols and carbon acids. On the other hand, the nucleophilic substitution reactions on the corresponding tosylate also afforded the same range of products 129, which proved more fruitful for secondary amines and thiols (Scheme 40, C).…”

Section: Scheme 35 Intramolecular Cyclization Reactions That Lead To ...mentioning

confidence: 99%

“…In 2016, the group of Paquin investigated two strategies using SF 5 ‐allylic alcohol 126 a as starting building block to attach the E ‐3‐(pentafluorosulfanyl)allyl chain onto various nucleophiles [92] . One strategy was using the palladium‐catalysed Tsuji–Trost coupling between allyl carbonate 128 and the desired nucleophiles, which was especially effective for phenols and carbon acids.…”

Section: Sf5‐building Blocks and Sf4‐bridged Precursors In Organic Sy...mentioning

confidence: 99%

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Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Kordnezhadian

Zogu

et al. 2022

Chemistry A European J

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Pentafluorosulfanyl (SF 5 )-containing compounds and corresponding analogs are a highly valuable class of fluorine-containing building blocks owing to their unique properties. The reason for that is the set of peculiar and tremendously beneficial characteristics they can impart on molecules once introduced onto them. Despite this, their application in distinct scientific fields remains modest, given the extremely harsh reaction conditions needed to access such compounds. The recent synthetic approaches via SÀ F, and CÀ SF 5 bond formation as well as the use of SF 5containing building blocks embody a "stairway-to-heaven" loophole in the synthesis of otherwise-inaccessible chemical scaffolds only a few years ago. Herein, we report and evaluate the properties of the SF 5 group and analogs, by summarizing synthetic methodologies available to access them as well as following applications in material science and medicinal chemistry since 2015.

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Section: Scheme 35 Intramolecular Cyclization Reactions That Lead To ...mentioning

confidence: 99%

Section: Sf5‐building Blocks and Sf4‐bridged Precursors In Organic Sy...mentioning

confidence: 99%

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Kordnezhadian

Zogu

et al. 2022

Chemistry A European J

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“…20 As shown in Scheme 5, the acyclic precursors 8 and 9 were prepared from pentafluoro(3-hydroxy-1-propenyl)sulfur (7) 21 using a two-step sequence that we reported recently. 22…”

Section: Feature Syn Thesismentioning

confidence: 99%

“…IR spectra were recorded on an FT-IR spectrophotometer. (E)-4,4,4-Trifluorobut-2-en-1-yl 4-methylbenzenesulfonate (2) 12b and (E)-3-(pentafluorosulfanyl)allyl 4-methylbenzenesulfonate 22 were prepared following literature procedures.…”

Section: Syn Thesismentioning

confidence: 99%

A Radical Access to CF3- and SF5-Containing Dihydrobenzofurans and Indolines

et al. 2017

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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.

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“…He has reported in the European Journal of Organic Chemistry on the introduction of fluorinated substituents onto nucleophiles. [7] Michael Organ (University of Ottawa) has been honored with the R. U. Lemieux Award, which is presented for distinguished contributions to the field organic chemistry. Organ studied at the University of Guelph, where he carried out his PhD (completed in 1992) with Gordon F. Lange.…”

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confidence: 99%

Chemical Institute of Canada and Canadian Society for Chemistry Awards 2016

2016

Angew Chem Int Ed

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TheC hemical Institute of Canada (CIC) and the Canadian Society for Chemistry (CSC) have honored several outstanding scientists in their 2016 awards program. We congratulate all the awardees including Mark Lautens (University of Toronto; CIC Catalysis Award), [1a] Stephen G. Withers (University of British Columbia;C IC Medal), [1b] Mark MacLachlan (University of British Columbia;CSC Award for Research Excellence in Materials Chemistry), [1a] and Federico Rosei (Institut National de la Recherche Scientifique,U niversitØ de QuØbec; CSC John C. Polyani Award), [1c] and feature those who have recently published in Angewandte Chemie and its sister journals. Kim M. Baines (Western University,Ontario) is the winner of the CIC MontrØal Medal/MØdaille de MontrØal, which is presented for distinguished contributions to the field of chemistry or chemical engineering.B aines studied at St. MarysU niversity,H alifax, and worked with Adrian G. Brook at the University of Toronto for her PhD (completed in 1987). From 1987-1988, she was ap ostdoctoral fellow with Wilhelm P. Neumann at the University of Dortmund (currently the Technische Universität Dortmund), and in 1988, she started her independent career at the University of Western Ontario (currently Western University). She was made professor in 2000 and is Vice-President of the CSC from June 2016 to May 2017. Baines and her research group are interested in the synthesis, reactivity,a nd spectroscopic characterization of low-valent main-group element compounds with novel bonding paradigms.S he has reported in Chemistry-A European Journal on cationic lowvalent gallium complexes of cryptand[2.2.2]. [2]Dennis G. Hall (University of Alberta) is the recipient of the Alfred Bader Award, which is given for excellent research in organic chemistry.H all carried out his PhD (completed in 1995

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Complementary Methods for the Introduction of the (E)‐3‐(Pentafluorosulfanyl)allyl Chain unto O‐, N‐, S‐, and C‐Based Nucleophiles

Cited by 9 publications

References 42 publications

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

Chemistry of Pentafluorosulfanyl Derivatives and Related Analogs: From Synthesis to Applications

A Radical Access to CF3- and SF5-Containing Dihydrobenzofurans and Indolines

Chemical Institute of Canada and Canadian Society for Chemistry Awards 2016

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