The Experts below are selected from a list of 276 Experts worldwide ranked by ideXlab platform
Dale L Boger - One of the best experts on this subject based on the ideXlab platform.
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fe iii nabh4 mediated free radical Hydrofluorination of unactivated alkenes
ChemInform, 2013Co-Authors: Timothy J Barker, Dale L BogerAbstract:The transformation is achieved under exceptionally mild conditions to yield the corresponding Markovnikov addition products.
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fe iii nabh4 mediated free radical Hydrofluorination of unactivated alkenes
Journal of the American Chemical Society, 2012Co-Authors: Timothy J Barker, Dale L BogerAbstract:A powerful Fe(III)/NaBH4-mediated free radical Hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical Hydrofluorination of alkenes, the Fe(III)/NaBH4-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH3CN/H2O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.
Jingli Zhang - One of the best experts on this subject based on the ideXlab platform.
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stereoselective one pot sequential dehydrochlorination trans Hydrofluorination reaction of β chloro α β unsaturated aldehydes or ketones facile access to z β fluoro β arylenals β fluoro β arylenones
Advanced Synthesis & Catalysis, 2017Co-Authors: Jingli Zhang, Junxin Duan, Lianghu Gu, Bifeng Chen, Yuefa GongAbstract:The monofluoroalkene substructure shows a high potential as a fluorinated synthon in organic synthesis. However, control of the Z/E stereoselectivity of multi-substituted monofluoroalkene products in one-pot reaction still remains a challenge. An unprecedented one-pot approach for the highly regio- and stereoselective preparation of functionalized (Z)-β-monofluoro tri-substituted alkenes from readily available β-chloro-α,β-unsaturated aldehydes or ketones has been explored. Mechanistic studies demonstrated the reaction initiated from dehydrochlorination of the substrates to give alkynyl aldehydes/ketones, followed by their trans-Hydrofluorination. It is worth mentioning that fluorinating reagent with suitable basicity and nucleophilicity plays a key role in promoting the formation of (Z)-β-fluoro-β-aryl tri-substituted monofluoroalkenes.
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Stereoselective One-Pot Sequential Dehydrochlorination/trans-Hydrofluorination Reaction of β-Chloro-α,β-unsaturated Aldehydes or Ketones: Facile Access to (Z)-β-Fluoro-β-arylenals/β-Fluoro-β-arylenones
Advanced Synthesis & Catalysis, 2017Co-Authors: Jingli Zhang, Junxin Duan, Lianghu Gu, Bifeng Chen, Yuefa GongAbstract:The monofluoroalkene substructure shows a high potential as a fluorinated synthon in organic synthesis. However, control of the Z/E stereoselectivity of multi-substituted monofluoroalkene products in one-pot reaction still remains a challenge. An unprecedented one-pot approach for the highly regio- and stereoselective preparation of functionalized (Z)-β-monofluoro tri-substituted alkenes from readily available β-chloro-α,β-unsaturated aldehydes or ketones has been explored. Mechanistic studies demonstrated the reaction initiated from dehydrochlorination of the substrates to give alkynyl aldehydes/ketones, followed by their trans-Hydrofluorination. It is worth mentioning that fluorinating reagent with suitable basicity and nucleophilicity plays a key role in promoting the formation of (Z)-β-fluoro-β-aryl tri-substituted monofluoroalkenes.
Sébastien Thibaudeau - One of the best experts on this subject based on the ideXlab platform.
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synthetic deoxynojirimycin derivatives bearing a thiolated fluorinated or unsaturated n alkyl chain identification of potent α glucosidase and trehalase inhibitors as well as f508del cftr correctors
Organic and Biomolecular Chemistry, 2015Co-Authors: V Cendret, Sébastien Thibaudeau, Thibaut Legigan, Agnes Mingot, Isao Adachi, Matilde Forcella, Paolo Parenti, J Bertrand, Frederic Becq, Caroline NorezAbstract:The synthesis of eleven 1-deoxynojirimycin (DNJ) derivatives presenting either a monofluoro, difluoro, thiolated or unsaturated N-alkyl chain of various length is described. Exploiting the unsaturated moiety on the nitrogen, fluorine has been introduced through a HF/SbF5 superacid catalysed Hydrofluorination and thiol–ene click chemistry allowed introduction of sulfur. The synthetic derivatives have been tested for their ability to inhibit glycosidases and correct F508del-CFTR. Two of the unsaturated iminosugars exhibited potency similar to Miglustat as F508del-CFTR correctors. The thioalkyl iminosugars as well as the corresponding alkyl iminosugars demonstrated low micromolar α-glucosidases and trehalases inhibition. Introduction of fluorine abolished F508del-CFTR correction and trehalase inhibition.
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Chemo- and stereoselective synthesis of fluorinated enamides from ynamides in HF/pyridine: second-generation approach to potent ureas bioisosteres.
Journal of Organic Chemistry, 2015Co-Authors: Benoît Métayer, Guillaume Compain, Kevin Jouvin, Agnès Martin-mingot, Christian Bachmann, Jérôme Marrot, Gwilherm Evano, Sébastien ThibaudeauAbstract:(E)- and (Z)-α-fluoroenamides could be easily prepared with high levels of chemo- and regioselectivities by Hydrofluorination of readily available ynamides with HF/pyridine. The scope and limitations of this new process for the Hydrofluorination of ynamides, as well as the stability of the resulting α-fluoroenamides, have been extensively studied. Theoretical calculations at the MP2 and B3LYP levels of theory showed that the resulting fluoroenamides exhibit geometrical and electronic properties that partially mirror those of ureas, therefore demonstrating that the Hydrofluorination of ynamides provides a general, straightforward, and user-friendly approach to bioisosteres of ureas, potent building blocks for biological studies and medicinal chemistry.
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stereoselective Hydrofluorination of ynamides a straightforward synthesis of novel α fluoroenamides
Chemical Communications, 2012Co-Authors: Guillaume Compain, Kevin Jouvin, Jérôme Marrot, Gwilherm Evano, Agnes Martinmingot, Sébastien ThibaudeauAbstract:α-Fluoroenamides, potent rigid fluorinated bioisosters of ureas, have been synthesized by a highly regio- and stereo-selective Hydrofluorination of ynamides in anhydrous HF. This reaction provides the first general entry to α-fluoroenamides and can easily be applied to a wide range of substrates.
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substitution effect on the Hydrofluorination reaction of unsaturated amines in superacid hf sbf5
Organic and Biomolecular Chemistry, 2009Co-Authors: Agnes Martinmingot, Mariepaule Jouannetaud, Omar Karam, Sébastien ThibaudeauAbstract:This paper describes the scope and limitations of the Hydrofluorination reaction in superacid HF/SbF5. On the basis of experimental studies of polyfunctional substrates’ behaviour, the dramatic effect of substitution on the superelectrophilic character of ammonium–carbenium dications was emphasized. This reaction was applied to the synthesis of novel fluorinated key building blocks. Furthermore, the Hydrofluorination reaction and the discovered homodimerization/fluorination reaction were applied to the synthesis of highly valued fluorinated diamines.
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a novel facile route to β fluoroamines by Hydrofluorination using superacid hf sbf5
Chemical Communications, 2007Co-Authors: Sébastien Thibaudeau, Agnes Martinmingot, Mariepaule Jouannetaud, Omar Karam, Fabien ZuninoAbstract:A range of unsaturated amines and sulfonamides were converted to β-fluoro nitrogen analogues after Hydrofluorination in superacidHF–SbF5, based on the formation of highly reactive electrophilic intermediates.
Timothy J Barker - One of the best experts on this subject based on the ideXlab platform.
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fe iii nabh4 mediated free radical Hydrofluorination of unactivated alkenes
ChemInform, 2013Co-Authors: Timothy J Barker, Dale L BogerAbstract:The transformation is achieved under exceptionally mild conditions to yield the corresponding Markovnikov addition products.
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fe iii nabh4 mediated free radical Hydrofluorination of unactivated alkenes
Journal of the American Chemical Society, 2012Co-Authors: Timothy J Barker, Dale L BogerAbstract:A powerful Fe(III)/NaBH4-mediated free radical Hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical Hydrofluorination of alkenes, the Fe(III)/NaBH4-mediated reaction is conducted under exceptionally mild reaction conditions (0 °C, 5 min, CH3CN/H2O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.
James E Thomson - One of the best experts on this subject based on the ideXlab platform.
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ring opening Hydrofluorination of 2 3 and 3 4 epoxy amines by hbf4 oet2 application to the asymmetric synthesis of s s 3 deoxy 3 fluorosafingol
Journal of Organic Chemistry, 2011Co-Authors: Alexander J Cresswell, Stephen G Davies, Melloney J Morris, Paul M Roberts, James E ThomsonAbstract:Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening Hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.
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Ring-Opening Hydrofluorination of 2,3- and 3,4-Epoxy Amines by HBF4·OEt2: Application to the Asymmetric Synthesis of (S,S)-3-Deoxy-3-fluorosafingol
Journal of Organic Chemistry, 2011Co-Authors: Alexander J Cresswell, Stephen G Davies, Melloney J Morris, Paul M Roberts, James E ThomsonAbstract:Treatment of a range of 2,3- and 3,4-epoxy amines with HBF4·OEt2 at room temperature results in fast and efficient SN2-type ring-opening Hydrofluorination to give stereodefined amino fluorohydrins. Operational simplicity, scalability, and short reaction time at ambient temperature are notable features of this method. The utility of this methodology is exemplified in a concise asymmetric synthesis of (S,S)-3-deoxy-3-fluorosafingol.
