- A Class of Amide Ligands Enable Cu-Catalyzed Coupling of (Hetero)aryl Halides with Sulfinic Acid Salts under Mild Conditions
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The amide derived from 4-hydroxy-l-proline and 2,6-dimethylaniline is a powerful ligand for Cu-catalyzed coupling of (hetero)aryl halides with sulfinic acid salts, allowing the formation of a wide range of (hetero)aryl sulfones from the corresponding (hetero)aryl halides at considerably low catalytic loadings. The coupling of (hetero)aryl iodides and sodium methanesulfinate proceeds at room temperature with only 0.5 mol % CuI and ligand, representing the first example for Cu-catalyzed arylation at both low catalytic loading and room temperature.
- Zhao, Jinlong,Niu, Songtao,Jiang, Xi,Jiang, Yongwen,Zhang, Xiaojing,Sun, Tiemin,Ma, Dawei
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p. 6589 - 6599
(2018/05/31)
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- Sulfide oxidation by O2: Synthesis, structure and reactivity of novel sulfide-incorporated Fe(II) bis(imino)pyridine complexes
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The unsymmetrical iron(II) bis(imino)pyridine complexes [Fe II(LN3SMe)(H2O)3](OTf)2 (1), and [FeII(LN3-SMe)Cl2] (2) were synthesized and their reactivity with O2 was examined. Complexes 1 and 2 were characterized by single crystal X-ray crystallography, LDI-MS, 1H NMR and elemental analysis. The LN3SMe ligand was designed to incorporate a single sulfide donor and relies on the bis(imino)pyridine scaffold. This scaffold was selected for its ease of synthesis and its well-precedented ability to stabilize Fe(II) ions. Complexes 1 and 2 ware prepared via a metal-assisted template reaction from the unsymmetrical pyridyl ketone precursor 2-(O=CMe)-6-(2,6-(iPr 2-C6H3N=CMe)-C5H3N. Reaction of 1 with O2 was shown to afford the S-oxygenated sulfoxide complex [Fe(LN3S(O)Me)(OTf)]2+ (3), whereas compound 2, under the same reaction conditions, afforded the corresponding sulfone complex [Fe(LN3S(O2)Me)Cl]2+ (4).
- Widger, Leland R.,Siegler, Maxime A.,Goldberg, David P.
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p. 179 - 189
(2013/07/26)
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- N-(phenylsulfonyl)picolinamide derivatives, process for producing the same, and herbicide
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A herbicide containing as the active ingredient an N-(henylsulfonyl)picolinamide derivative represented by general formula (I) wherein X reprcsents a halogeno, a C1-4 alkyl, a C1-4 haloalkyl, a C1-4 alkoxy, a C1-4 haloalkoxy, a (C1-4 alkoxy)carbonyl, a [di(C1-4 alkyl)amino]sulfonyl, an [N—(C1-4 alkyl)-N—(C1-4 alkoxy)amino]sulfonyl, a (C1-4 alkylamino)sulfonyl, a C1-4 alkylthio, a C1-4 alkylsulfinyl, a C1-4 alkylsulfonyl, or nitro; n is an integer of 0 to 5; Y represets a halogeno, a C1-4 alkyl, a C1-4 haloalkyl, a C1-4 alkoxy, C1-4 haloalkoxy, a C1-4 alkylthio, a C1-4 haloalkylthio, amino, a C1-4 alkylamino, a di(C1-4 alkyl)amino, a (C1-4 alkoxy) C1-4 alkyl, a (C1-4 alkylthio) C1-4 alkyl, or nitro; and m is an integer of 0 to 4. This active ingredient is synthesized by condensing a substituted picolinic acid with a substituted benzenesulfonamide under dehydration, or by reacting the phenyl ester of a substituted picolinic acid with a substituted benzenesulfonamide in the presence of a basic compound.
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- Process for the preparation of 2-[alkyl(aryl)]sulfonylbenzene-sulfonyl chlorides and their intermediates
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A process for the preparation of 2-[alkyl(aryl)]sulfonylbenzene sulfonyl chlorides of the following formula is provided: in which R is alkyl or aryl substituted at the ortho or meta positions with alkyl, aryl, NHAc or alkoxy, comprising the steps of: a) r
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- Endocyclic Nucleophilic Substitution at Tetracoordinate Sulfur(VI)
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A search for endocyclic nucleophilic substitution at tetracoordinate sulfur(VI), usually sulfonyl sulfur, was carried out through the use of molecules so constructed that any intramolecular substitution process was forced to proceed through four-, five-,
- Andersen, Kenneth K.,Chumpradit, Sumalee,McIntyre, Debra J.
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p. 4667 - 4675
(2007/10/02)
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- DECOMPOSITION OF ARILAZIDES AND P-TOSYLAZIDE BY THF/n-BUTYLLITHIUM. A NEW SOURCE OF DIAZOMETHANE
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Variously substituted arylazides, as well as p-tosylazide, when allowed to react at room temperature with THF previously treated with n-butyllithium, undergo a rapid decomposition affording the corresponding amines and formamides, together with diazomethane.This diazo transfer (with deformylation) reaction is thought to involve the enolate of the acetaldehyde generated by the known cycloreversion of THF in the presence on n-butyllithium.
- Babudri, F.,Di Nunno, L.,Florio, S.,Valzano, S.
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p. 1731 - 1736
(2007/10/02)
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- 149. Notizen zur Synthese von 2-Aminophenylsulfonen
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Syntheses of the alkyl, cycloalkyl and aryl 2-aminophenyl sulfones 10 were achieved by oxidation of the corresponding 2-nitrophenyl sulfides 7 to the 2-nitrophenyl sulfones 9 followed by ethanolic Bechamp-reduction.The sulfides 7 in turn were obtained by either reactions of 2-nitro-thiophenol (8) with the appropriate alkyl and cycloalkyl halides or of 2-chloro-nitrobenzene (5) with the relevant thiols.Condensation of 2-nitrobenzenesulfinic acid (3) with bromoacetic acid in aqueous alkaline solution led - presumably via 2-nitrophenylsulfonylacetic acid (4) - to methyl2-nitrophenyl sulfone (1), reduction of which gave 2-aminophenyl methyl sulfone (2).Treatment of 2-aminothiophenol (11) with t-butyl alcohol in aqueous sulfuric acid gave 2-aminophenyl t-butyl sulfide (12), which was acetylated to o-t-butylthio-acetanilide (13).Oxidation of the latter to o-t-butylsulfonyl-acetanilide (14) followed by hydrolysis led to 2-aminophenyl t-butyl sulfone (15).
- Courtin, Alfred,Tobel, Hans-Rudolf von,Auerbach, Guenther
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p. 1412 - 1419
(2007/10/02)
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