- Visible-light-promotedE-selective synthesis of α-fluoro-β-arylalkenyl sulfidesviathe deoxygenation/isomerization process
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Regioselective synthesis of α-fluoro-β-arylalkenyl sulfides has been established withgem-difluoroalkenes and sodium sulfinates in a transition-metal-free manner. A series of control experiments were executed to demonstrate thiol radicals and anions as the proposed intermediates. Notably, regioselectiveZ→Eisomerization was achieved under green light irradiation in the absence of a photoinitiator.
- Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
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supporting information
p. 2152 - 2155
(2021/03/06)
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- Highly E-Selective Synthesis of α-Fluoro-β-arylalkenyl Sulfones from gem-Difluoroalkenes with Sodium Sulfinates
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The straightforward synthesis of α-fluoro-β-arylalkenyl sulfones under transition-metal-and base-free conditions has been described, which displays broad functional group compatibility and high stereoselectivity. In particular, the strategy is also applied to the late-stage modification of complex natural products and drugs.
- Li, Yuxiu,Li, Xiangqian,Li, Xiaowei,Shi, Dayong
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p. 6983 - 6993
(2021/05/06)
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- Metal-Free Access to (E/Z)-α-Fluorovinyl Phosphorus Compounds from gem-Difluorostyrenes
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A facile and efficient method for the synthesis of (E/Z)-α-fluorovinyl phosphorus compounds from gem-difluorostyrenes with diphenylphosphine oxide/dialkyl phosphate and DBU at room temperature was developed. A series of 1-fluorovinyl phosphine oxides/phosphonates were obtained with moderate to excellent yields in these reactions. Additionally, most isomers (E/Z type) of the target compounds could be easily separated and purified by column chromatography.
- Peng, Yingyuan,Zhang, Xiaofei,Qi, Xueyu,He, Qian,Zhang, Bin,Hao, Jian,Yang, Chunhao
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p. 1170 - 1177
(2019/01/16)
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- Palladium-Catalyzed Direct Approach to α-Trifluoromethyl Alcohols by Selective Hydroxylfluorination of gem-Difluoroalkenes
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A novel palladium-catalyzed selective hydroxylfluorination of gem-difluoroalkenes has been developed. By employing easily obtainable gem-difluoroalkenes and NFSI as the fluorine source, the scope, advantages, and limitations of this reaction were investigated. The reaction presents an efficient synthesis to afford a series of α-trifluoromethyl alcohols in good to excellent yields. Furthermore, this reaction probably proceeds via oxidation of Pd0 to PdII fluoride complex by NFSI, followed by fluoropalladation of gem-difluoroalkenes to generate an α-trifluoromethylbenzyl–Pd intermediate. And this strategy offers more possibilities for the construction of other bonds, such as C–C, C–N and C–S.
- Zhang, Bin,Zhang, Xiaofei,Hao, Jian,Yang, Chunhao
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p. 5007 - 5015
(2018/10/05)
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- Nucleophilic difluoromethylation of aromatic aldehydes using trimethyl(trifluoromethyl)silane (TMSCF3)
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Reaction of the Ruppert–Prakash reagent (Me3SiCF3) with aromatic aldehydes in the presence of triphenylphosphine, lithium iodide and lithium tetrafluoroborate selectively furnishes gem-difluorinated phosphonium salts. Simple alkaline
- Krishnamoorthy, Sankarganesh,Kar, Sayan,Kothandaraman, Jotheeswari,Prakash, G.K. Surya
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- Difluoromethyl 2-pyridyl sulfone: A new gem-difluoroolefination reagent for aldehydes and ketones
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Chemical equation presented Difluoromethyl 2-pyridyl sulfone, a previously unknown compound, was found to act as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. It was found that the fluorinated sulfinate intermediate in the reaction is relatively stable, which can be observed by 19F NMR and trapped with CH 3l.
- Zhao, Yanchuan,Huang, Weizhou,Zhu, Lingui,Hu, Jinbo
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supporting information; experimental part
p. 1444 - 1447
(2010/06/20)
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