- Togni-II Reagent Mediated Selective Hydrotrifluoromethylation and Hydrothiolation of Alkenes?
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Based on the redox reactions of Togni-II reagent and thiols, a thiol-tuned selective functionalization of unactivated olefins was disclosed. In combination with aryl thiols, stoichiometric amount of Togni-II reagent prompted a hydrotrifluoromethylation of alkenes, in which, aryl thiols played as reductant and hydrogen source; while by utilization of alkyl thiols, catalytic amount of Togni-II reagent initiated thiol-ene and thiol-yne reactions. The reported applications are characterized by their operational simplicity and wide functional group tolerance.
- Teng, Shuang,Meng, Lingkui,Xu, Bingbing,Tu, Guangsheng,Wu, Peng,Liao, Zhiwen,Tan, Yulin,Guo, Jian,Zeng, Jing,Wan, Qian
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supporting information
p. 3429 - 3434
(2021/11/08)
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- Electrochemical Trifluoromethylation of Thiophenols with Sodium Trifluoromethanesulfinate
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We developed an electrochemical trifluoromethylation of thiophenols without the use of metal catalysts and oxidants. This reaction features mild reaction conditions, readily available substrate, as well as moderate to good yields. In addition, this protocol can be easily scaled up with moderate efficiency.
- Zhu, Xing-Xing,Wang, Huai-Qin,Li, Chen-Guang,Xu, Xiao-Lan,Xu, Jun,Dai, Jian-Jun,Xu, Hua-Jian
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p. 16114 - 16120
(2021/02/03)
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- PEST CONTROL COMPOSITION AND USE THEREFOR
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PROBLEM TO BE SOLVED: To provide a pest control composition having an excellent control effect on pests such as ixodid and flea. SOLUTION: A pest control composition contains a condensed heterocyclic compound represented by formula (1), and at least one p
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Paragraph 0174
(2019/02/14)
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- Silver-catalyzed fluoroalkylation of thiols using fluoroalkanesulfinates
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A practical sliver-catalyzed fluoroalkylation of aryl-, heteroaryl- and alkylthiols has been developed. The reaction has a good functional-group tolerance and excellent selectivity. A variety of stable and solid fluoroalkanesulfinates including di- and perfluoroalkanesulfinates can be employed. This methodology provides a straightforward and streamlined access to perfluoroalkylthiolated organic molecules. [Figure presented]
- Ma, Jing-jing,Liu, Qi-ran,Lu, Guo-ping,Yi, Wen-bin
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supporting information
p. 113 - 117
(2017/01/03)
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- Sandmeyer-Type Trifluoromethylthiolation and Trifluoromethylselenolation of (Hetero)Aromatic Amines Catalyzed by Copper
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Aromatic and heteroaromatic diazonium salts were efficiently converted into the corresponding trifluoromethylthio- or selenoethers by reaction with Me4NSCF3 or Me4NSeCF3, respectively, in the presence of catalytic amounts of copper thiocyanate. These Sandmeyer-type reactions proceed within one hour at room temperature, are applicable to a wide range of functionalized molecules, and can optionally be combined with the diazotizations into one-pot protocols.
- Matheis, Christian,Wagner, Victoria,Goossen, Lukas J.
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supporting information
p. 79 - 82
(2016/01/25)
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- Trifluoromethylthiolation of Unsymmetrical λ3-Iodane Derivatives: Additive-Free, Selective and Scalable Introduction of the SCF3 Group
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The reaction of copper trifluoromethyl sulfide with diaryliodonium salts provides a straightforward pathway for the synthesis of aryl trifluoromethyl thioethers under mild reaction conditions and within short reaction times. High chemoselectivity was achieved by using mesityl as a leaving group. A large range of novel [(het)aryl](mesityl)iodonium salts underwent this reaction under the optimized conditions to give the desired products in moderate to good yields.
- Nikolaienko, Pavlo,Yildiz, Tülay,Rueping, Magnus
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p. 1091 - 1094
(2016/03/05)
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- PEST CONTROL COMPOSITION AND USE THEREFOR
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PROBLEM TO BE SOLVED: To provide a pest control composition that is effective in controlling pests. SOLUTION: The pest control composition comprises a condensed heterocyclic compound represented by formula (1), and one or more agrochemical active ingredie
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Paragraph 0232
(2016/10/09)
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- Mild and Soft Catalyzed Trifluoromethylthiolation of Boronic Acids: The Crucial Role of Water
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The most reactive 2nd generation of trifluoromethanesulfenamides undergoes a copper-catalyzed cross-coupling reaction with boronic acids to afford CF3S-molecules. Contrary to the previous methods in the literature, no base addition, no heating, and no large excess of reagents are required to obtain good results. Furthermore, a crucial role of a small amount of water to favor this reaction has been demonstrated. This constitutes the mildest described conditions for such a reaction.
- Glenadel, Quentin,Alazet, Sébastien,Tlili, Anis,Billard, Thierry
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supporting information
p. 14694 - 14698
(2015/10/19)
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- A mild and fast photocatalytic trifluoromethylation of thiols in batch and continuous-flow
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S-CF3 bonds are important structural motifs in various pharmaceutical and agrochemical compounds. However, their preparation remains a major challenge in synthetic organic chemistry. Here, we report the development of a mild and fast photocatalytic trifluoromethylation of thiols. The combination of commercially available Ru(bpy)3Cl2, visible light and inexpensive CF3I gas proved to be an efficient method for the direct trifluoromethylation of thiols. The protocol is demonstrated on a wide range of aromatic, hetero-aromatic and aliphatic substrates in both batch and continuous microflow (32 examples, 52-98% yield). Process intensification through continuous microflow application resulted in a 15-fold increase in production rate (0.25 mmol min-1) due to improved gas-liquid mass transfer, enhanced irradiation as well as convenient handling of the gaseous CF3 source. Furthermore, the efficiency of the flow process allowed to reduce the amount of CF3I (1.1 equivalent) to reach full conversion. This journal is
- Straathof, Natan J. W.,Tegelbeckers, Bart J. P.,Hessel, Volker,Wang, Xiao,Nol, Timothy
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p. 4768 - 4773
(2015/01/09)
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- Recent advances in electrophilic CF3-transfer using hypervalent iodine(III) reagents
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The development of new methodologies for an efficient introduction of CF3 groups into complex molecules constitutes one of the most challenging tasks of modern organic chemistry. Recently, we reported the access to a new class of electrophilic CF3-transfer reagents based on hypervalent iodine. The versatile application of these reagents to C-centred nucleophiles, such as β-keto esters, silyl enol ethers and α-nitro esters, as well as to thiols and primary and secondary phosphines is described. Experiments with phenols afforded corresponding trifluomethylethers in very low yields. Schweizerische Chemische Gesellschaft.
- Kieltsch, Iris,Eisenberger, Patrick,Stanek, Kyrill,Togni, Antonio
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scheme or table
p. 260 - 263
(2009/04/07)
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- Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent
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Inexpensive, recyclable, and activable: these are the features of a new mild electrophilic trifluoromethylation reagent that can be used to transfer a CF3 group to C-centered nucleophiles, such as β-keto esters and α-nitro esters, and to S-centered nucleophiles (see scheme). (Chemical Equation Presented).
- Kieltsch, Iris,Eisenberger, Patrick,Togni, Antonio
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p. 754 - 757
(2007/10/03)
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- Heterocyclic compounds
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The invention provides compounds of formula (I) having nematicidal, insecticidal, acaricidal and fungicidal properties, compositions comprising them and processes and intermediates for their preparation: STR1 wherein: X is oxygen or sulphur; n is 0, 1 or 2; R1, R2, R3, and R4 are as described in the specification.
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- Chemistry of Halogenoperfluoroalkanes> Synthesis of Fluorinated Ethers and Thioethers via Radical or Anionic Intermediates
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Condensation of bromotrifluoromethane with potassium thiophenoxides in DMF is performed under pressure (2-3 atm) in a glass apparatus.Inhibition by nitrobenzene shows that a SRN1 mechanism is involved in the formation of aryl trifluoromethyl sulfides.Dichlorodifluoromethane itself reacts through a similar process to give aryl chlorodifluoromethyl sulfides.Condensation of 1,1,2-trichlorotrifluoroethane with potassium thiophenoxide or phenoxide occurs even in the presence of nitrobenzene.The formation of aryl 2,2-dichloro-1,1,2-trifluoroethyl sulfides or ethers can be explained by a chain carbanionic mechanism.
- Wakselman, Claude,Tordeux, Marc
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p. 4047 - 4051
(2007/10/02)
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