- Manganese-catalyzed cross-coupling of thiols with aryl iodides
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A manganese-catalyzed cross-coupling reaction of thiols with aryl iodides, furnishing aryl thioethers in good to excellent yields has been reported; the system shows good functional group tolerance and enables the sterically demanding aryl iodides to couple with thiols. Coming up for ArI: A manganese-catalyzed cross-coupling reaction of thiols with aryl iodides that furnishes aryl thioethers in good to excellent yields has been reported. Functional groups such as unprotected alcohols and chloro substituents are tolerated under these reaction conditions. Moreover, this catalytic system enables the sterically demanding aryl iodides to couple with thiols (see scheme; R=aryl or alkyl).
- Liu, Tsung-Jui,Yi, Chih-Lun,Chan, Chien-Ching,Lee, Chin-Fa
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p. 1029 - 1034
(2013/08/25)
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- A very active Cu-catalytic system for the synthesis of aryl, heteroaryl, and vinyl sulfides
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Figure presented cis-1,2-Cyclohexanediol (L3) has been shown to be an efficient and versatile bidentate O-donor ligand that provides a highly active Cu-catalytic system. It was more effective than diols such as trans-1,2-cyclohexanediol or ethylene glycol. This commercially available cis-1,2-cyclohexanediol ligand facilitated the Cu-catalyzed cross-coupling reactions of alkyl, aryl, or heterocyclic thiols with either alkyl, aryl, heterocyclic, or substituted vinyl halides. This new catalytic system promoted the mild and efficient stereo- and regiospecific synthesis of biologically important vinyl sulfides. The yields obtained using electron-rich substituted vinyl sulfides with this catalyst system are generally 75-98%. Most importantly, this singular catalyst system is extremely versatile and provides entry into a wide range of sulfides. This method is particularly noteworthy given its mild reaction conditions, simplicity, generality, and exceptional level of functional group tolerance.
- Kabir, M. Shahjahan,Lorenz, Michael,Van Linn, Michael L.,Namjoshi, Ojas A.,Ara, Shamim,Cook, James M.
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experimental part
p. 3626 - 3643
(2010/07/14)
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- COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS
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One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.
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- A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols
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(matrix presented) An efficient copper-catalyzed carbon-sulfur bond formation reaction was developed. This method is particularly noteworthy given its experimental simplicity, high generality, and exceptional level of functional group toleration and the low cost of the catalyst system.
- Kwong, Fuk Yee,Buchwald, Stephen L.
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p. 3517 - 3520
(2007/10/03)
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- Derivatives of hydroxyphenylsulfanylbenzoic and hydroxphenylsulfanylarylacetic acids
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Processes for the preparation of derivatives of hydroxyphenylsulfanylbenzoic and hydroxyphenylsulfanylarylacetic acids of Formula (I) and pharmaceutical compositions including these compounds are provided: wherein X is H, halogen or NO2group, n is 0 or 1, and m is 2 to 4 if Z is either 4-acetyl-3 -hydroxy-2-propylphenoxy of Formula (II): or a piperazinyl residue, or m is 1 if Z is quinolin-2-yl or 6-chloroquinoli-2-yl.
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