Facile Thiol–Ene Click Protocol Using Benzil as Sensitizer and White LED as Light Source
The thiol–ene reaction leading to a series of thioether derivatives by simple metal and oxidant free visible light promoted photosensitized protocol, following anti-Markonikov hydrothiolation of unactivated aryl and alkyl olefins at room temperature is demonstrated. Benzil served as a green photosensitizer in this reaction and white LED lights as a light source. This radical based thiol–ene reaction is operationally simple and tolerates a wide variety of functional groups present in olefins.
Das, Anupam,Thomas, K. R. Justin
supporting information
p. 7214 - 7218
(2020/11/30)
Lewis acid activation of pyridines for nucleophilic aromatic substitution and conjugate addition
A clean, mild and sustainable method for the functionalization of pyridines and their analogues is reported. A zinc-based Lewis acid is used to activate pyridine and its analogues towards nucleophilic aromatic substitution, conjugate addition, and cyclization reactions by binding to the nitrogen on the pyridine ring and activating the pyridine ring core towards further functionalization.
Abou-Shehada, Sarah,Teasdale, Matthew C.,Bull, Steven D.,Wade, Charles E.,Williams, Jonathan M. J.
p. 1083 - 1087
(2015/03/30)
Amberlyst-15: An efficient heterogeneous reusable catalyst for selective anti-Markovnikov addition of thiols to alkenes/alkynes and for thiolysis of epoxides
The anti-Markovnikov addition of thiols to alkenes/alkynes and thiolysis of epoxides is described using Amberlyst-15 as a selective, commercially available, inexpensive and reusable catalyst. The products like diorganyl sulphides, β-hydroxy sulphides and phenyl(styryl)sulfanes were obtained in good to excellent yields in short reaction time and with high regio-selectivity. The catalyst was reused up to five consecutive recycles without any loss in its catalytic activity. The developed methodology is a metal free protocol for C-S bond formation reaction with high atom economy.
Lanke, Satish R.,Bhanage, Bhalchandra M.
p. 29 - 33
(2013/08/23)
METHOD FOR PRODUCING THIOETHER COMPOUND
Disclosed is an efficient and widely-applicable method for commercially producing a thioether compound or a thiol compound which is useful as a pharmaceutical compound or a production intermediate of it. Specifically disclosed is a method for producing a thioether compound represented by the general formula [I] below or a salt thereof. This method is characterized in that a compound represented by the following general formula [III]: [III] (wherein X represents a bromine atom, a chlorine atom or a trifluoromethylsulfonyloxy group, and ring A represents an aryl group or a heteroaryl ring group) or a salt thereof is reacted with a thiol compound represented by the following general formula [II]: [II] or a salt thereof in the presence of a palladium compound such as Pd2(dba)3, a base such as i-Pr2NEt and a phosphorus compound represented by the following formula [AA].
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(2008/06/13)
METHOD FOR PRODUCING THIOETHER COMPOUND
Disclosed is an efficient and widely-applicable method for commercially producing a thioether compound or a thiol compound which is useful as a pharmaceutical product or a production intermediate of a pharmaceutical product. Specifically disclosed is a method for producing a thioether compound represented by the general formula [I] below or a salt thereof. This method is characterized in that a compound represented by the following general formula [III]: [III] (wherein X represents a bromine atom, a chlorine atom or a trifluoromethylsulfonyloxy group, and ring A represents an aryl group or a heteroaryl ring group) or a salt thereof is reacted with a thiol compound represented by the following general formula [II]: [II] or a salt thereof in the presence of a palladium compound such as Pd2(dba)3, a base such as i-Pr2NEt and a phosphorus compound represented by the following formula [AA].
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Page/Page column 45; 57-58
(2008/06/13)
A general palladium-catalyzed coupling of aryl bromides/triflates and thiols
(Chemical equation presented) We have developed an efficient palladium-catalyzed carbon-sulfur bond formation reaction of aryl bromides, triflates, and activated aryl chloride. Using this protocol, we have shown tolerance to a wide variety of aryl thiols and alkyl thiols that can also be used as sulfide equivalents.
Itoh, Takahiro,Mase, Toshiaki
p. 4587 - 4590
(2007/10/03)
2-(4-Pyridyl)ethyl as a Protective Group for Sulfur Functionality
2-(4-Pyridyl)ethyl sulfides have been prepared from a variety of alkyl and aryl thiols and from alkyl and acyl halides.These sulfides and their corresponding sulfoxides and sulfones were each depyridylethylated by quaternization and subsequent treatment with mild base to give respectively the thiols, sulfenic acids, sulfinic acids, and sulfenamides.During one of these protection-deprotection sequences, methyl 1-octyl sulfoxide was readily converted by aerial oxidation into the corresponding sulfone.
Katritzky, Alan R.,Takahashi, Ichiro,Marson, Charles M.
p. 4914 - 4920
(2007/10/02)
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