2018
DOI: 10.1021/acscatal.8b01330
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Fluorobissulfonylmethyl Iodides: An Efficient Scaffold for Halogen Bonding Catalysts with an sp3-Hybridized Carbon–Iodine Moiety

Abstract: The halogen-bond donors FBSM-I and FBDT-I, which contain an sp3-hybridized carbon–iodine (Csp3 –I) moiety, were designed and synthesized. The highly electron-withdrawing nature of the fluorobissulfonyl-methane scaffold leads to the generation of σ-holes on the surface of the iodine atoms in FBSM-I and FBDT-I. Mukaiyama aldol reactions and hydrogen-transfer reductions are efficiently catalyzed by FBSM-I and FBDT-I under neutral and mild reaction conditions. The driving force for these transformations should be … Show more

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Cited by 39 publications
(34 citation statements)
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“…The reduction of reaction barrier of hydrocyanation reaction of imine by 4-10 kcal/mol via XB catalysis using various fluoroiodobenzenes (9-12) seems to be a remarkable result, given their monodentate nature. Experimentally, only in a very few cases were monodentate XB compounds found to be catalytic [16,26,70]. However, these calculations were performed without considering the effect of entropy (see Table 1), which cannot be ignored when comparing catalyzed to uncatalyzed reactions.…”
Section: Computational Study Of Xb-catalyzed Hydrocyanation Of Iminesmentioning
confidence: 99%
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“…The reduction of reaction barrier of hydrocyanation reaction of imine by 4-10 kcal/mol via XB catalysis using various fluoroiodobenzenes (9-12) seems to be a remarkable result, given their monodentate nature. Experimentally, only in a very few cases were monodentate XB compounds found to be catalytic [16,26,70]. However, these calculations were performed without considering the effect of entropy (see Table 1), which cannot be ignored when comparing catalyzed to uncatalyzed reactions.…”
Section: Computational Study Of Xb-catalyzed Hydrocyanation Of Iminesmentioning
confidence: 99%
“…Reduction of quinoline by Hantzsch ester is an important organic reaction that was explored many times in the literature as a benchmark reaction for new XB catalysts [16,21,26]. In 2014, Tan et al reported that iodoimidazolinium compound (39) (Scheme 4) can catalyze the reduction of quinoline by Hantzsch ester to give 91% yield in dichloromethane at room temperature.…”
Section: Xb-catalyzed Reduction Of Quinolines By Hantzsch Estermentioning
confidence: 99%
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“…In 2008, Bolm showed that haloperfluoroalkanes can be used as XB catalysts for the reduction of 2-phenylquinoline 10 using HE [47]. Since then, this reduction has often been used as a benchmark reaction to evaluate the activity of XB [48,49] and ChB [15,16] catalysts.…”
Section: Catalysismentioning
confidence: 99%
“…reported XB‐donor‐catalyzed reduction of quinolines by Hantzsch esters . After this seminal work, other catalytic reactions were successfully developed for the activation of lone‐pair‐possessing heteroatoms (Y) in the substrates (e.g., imine derivatives, carbonyl compounds, alkyl halides, thioamides, iodonium ylides, and N‐haloamides; Figure B, left). In contrast to activation of the lone pair (n‐electron) of heteroatoms, catalyst development of XB for the activation of π‐electrons (C−X⋅⋅⋅π XB) has not been explored, although C−X⋅⋅⋅π XB interactions have been reported in crystal engineering and biomolecular systems (Figure B, right).…”
Section: Figurementioning
confidence: 99%