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This invention is directed to a five step regio-specific synthesis of 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylic acid compound of formula 16 comprising the steps of acetalating 3-methyl-thiophene-2-carbaldehyde in an alcohol solvent; iodinating the acetalated 3-methyl-thiophene-2-carbaldehyde in an non-protic polar or hydrocarbon solvent to yield the corresponding iodinated and acetalated 3-methyl-thiophene-2-carbaldehyde product; treating the iodinated and acetalated product with water to yield the corresponding 5-iodo-3-methyl-thiophene-2-carbaldehyde; oxidizing the 5-iodo-3-methyl-thiophene-2-carbaldehyde to the corresponding 5-iodo-3-methyl-thiophene-2-carboxylic acid in ketone solvent; Ullmann coupling of the 5-iodo-3-methyl-thiophene-2-carboxylic acid with alkali metal propoxide salt using a copper catalyst in propanol to yield 3-methyl-5-propoxy-thiophene-2-carboxylic acid; esterifying 3-methyl-5-propoxy-thiophene-2-carboxylic acid to yield the corresponding alkyl 3-methyl-5-propoxy-thiophene-2-carboxylate; brominating the 3-methyl-5-propoxy-thiophene-2-carboxylic acid to yield the corresponding alkyl 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylate; and basic hydrolyzing the alkyl 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylate with base to yield 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylic acid.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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We present an energy band model and a method for filling p-type CuSCN in n-type porous TiO2 film. The energy band model is based on the interface energy levels between TiO2/CuSCN heterojunction and the aqueous electrolyte. The whole deposition process is divided into three stages: the uniform nucleation on the internal surface at positive potential, the crystal growth with the cathodic potential shifting negatively and the thermal activated growth at constant potential. This was demonstrated by the electrochemical experiment combining the hydrothermal process. It was found that the obtained TiO2/CuSCN heterojunction exhibited good rectification characteristics, indicating that an intimate electrical contact was formed between the large internal surface of TiO2 film and CuSCN. This novel hydrothermal-electrochemical method may be valuable for fabricating extremely thin absorber (eta)-solar cells and other semiconductor devices.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Reaction of copper(I) thiocyanate and triphenylphosphane with the bidentate Schiff base N,N?-bis(trans-2-nitrocinnamaldehyde)ethylenediamine {Nca2en, (1); systematic name (1E,1?E,2E,2?E)-N,N?-(ethane-1,2-diyl)bis[3-(2-nitrophenyl)prop-2-en-1-imine]}, C20H18N4O4, in a 1:1:1 molar ratio in acetonitrile resulted in the formation of the complex {(1E,1?E,2E,2?E)-N,N?-(ethane-1,2-diyl)bis[3-(2-nitrophenyl)prop-2-en-1-imine]-kappa2 N,N?}(thiocyanato-kappaN)(triphenylphosphane-kappaP)copper(I)], [Cu(NCS)(C20H18N4O4)(C18H15P)] or [Cu(NCS)(Nca2en)(PPh3)], (2). The Schiff base and copper(I) complex have been characterized by elemental analyses, IR, electronic and 1H NMR spectroscopy, and X-ray crystallography [from synchrotron data for (1)]. The molecule of (1) lies on a crystallographic inversion centre, with a trans conformation for the ethylenediamine unit, and displays significant twists from coplanarity of its nitro group, aromatic ring, conjugated chain and especially ethylenediamine segments. It acts as a bidentate ligand coordinating via the imine N atoms to the CuI atom in complex (2), in which the ethylenediamine unit necessarily adopts a somewhat flattened gauche conformation, resulting in a rather bowed shape overall for the ligand. The NCS- ligand is coordinated through its N atom. The geometry around the CuI atom is distorted tetrahedral, with a small N-Cu-N bite angle of 81.56(12) and an enlarged opposite angle of 117.29(9) for SCN-Cu-P. Comparisons are made with the analogous Schiff base having no nitro substituents and with metal complexes of both ligands.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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The versatile coordination behavior of the PNP ligands 1A (2,6-bis[(di-tert-butylphosphino)methyl]pyridine) and 1B (2,6- bis[(diphenylphosphino)methyl]pyridine) to CuI is described, whereby a hemilabile interaction of the pyridine N-donor atom to the copper center resulted in a rare T-shaped complex with 1A, while with 1B also a tetracoordinated species could be isolated. Theoretical calculations support the weak interaction of the pyridine N donor in 1A with the Cu center.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Diabetes is one of the most common disorders that substantially contributes to an increase in global health burden. As a metabolic disorder, diabetes is associated with various medical conditions and diseases such as obesity, hypertension, cardiovascular diseases, and atherosclerosis. In this review, we cover the scientific studies on sodium/glucose cotransporter (SGLT) inhibitors published during the last decade. Our focus on providing an exhaustive overview of SGLT inhibitors enabled us to present their chemical classification for the first time.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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The addition of Yb(OTf)3 (10 mol%) in a Rh2(OAc)4-catalyzed reaction of o-(methoxycarbonyl)-alpha-diazoacetophe-none with N-methylmaleimide in CH2Cl2 or in diethyl ether gave cycloadducts with high endo-selectivity (endo:exo = 95:5-96:4). The CuOTf (20 mol%)-or CuCl-Yb(OTf)3 (5 mol%)-catalyzed reaction also gave 1,3-dipolar cycloadducts in an endo-selective manner (endo:exo = 94:6). On the other hand, a reaction using only Rh2(OAc)4 (5 mol%) as the catalyst in benzene under reflux gave cycloadducts with exo-selectivity (endo:exo = 11:89). The reaction of N-ethyland N-phenylmaleimides under the same conditions showed a similar tendency in terms of the stereoselectivity.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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The present application is directed to a coating composition comprising a ceramic binder and inorganic copper compound particles. Generally, the inorganic copper compound particles have a median particle size of less than 5 micrometers. In some embodiments, the particles have a median particle size of greater than 1 micrometer. The inorganic copper compound particles may be non-photocatalytic. The coating may also be placed on a structural layer.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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The new area of lithio(thiocyanato)cuprates has been developed. Using inexpensive, stable and safe CuSCN for their preparation, these complexes revealed Lipshutz-type dimeric motifs with solvent-dependent point group identities; planar, boat-shaped and chair shaped conformers are seen in the solid state. In solution, both Lipshutz-type and Gilman structures are clearly seen. Since the advent in 2007 of directed ortho cupration, effort has gone into understanding the structure-reactivity effects of amide ligand variation in and alkali metal salt abstraction from Lipshutz-type cuprates such as (TMP)2Cu(CN)Li2(THF) 1 (TMP = 2,2,6,6-tetramethylpiperidide). The replacement of CN- with SCN- is investigated presently as a means of improving the safety of lithium cuprates. The synthesis and solid state structural characterization of reference cuprate (TMP)2Cu(CN)Li2(THP) 8 (THP = tetrahydropyran) precedes that of the thiocyanate series (TMP)2Cu(SCN)Li2(L) (L = OEt29, THF 10, THP 11). For each of 9-11, preformed TMPLi was combined with CuSCN (2 : 1) in the presence of sub-stoichiometric Lewis base (0.5 eq. wrt Li). The avoidance of Lewis basic solvents incurs formation of the unsolvated Gilman cuprate (TMP)2CuLi 12, whilst multidimensional NMR spectroscopy has evidenced the abstraction of LiSCN from 9-11 in hydrocarbon solution and the in situ formation of Gilman reagents. The synthetic utility of 10 is established in the selective deprotometalation of chloropyridine substrates, including effecting transition metal-free homocoupling in 51-69% yield.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Chemical engineers work across a number of sectors, processes differ within each of these areas, but chemistry and chemical engineering roles are found throughout, creation and manufacturing process of chemical products and materials. HPLC of Formula: Cu2O, Name is Copper(I) oxide, HPLC of Formula: Cu2O, molecular formula is Cu2O. In a article,once mentioned of HPLC of Formula: Cu2O

Phenyl-substituted perfluoroalkanesulfonanilides in which the phenyl rings are linked by sulfur, sulfinyl or sulfonyl and salts thereof in which the rings and the perfluoroalkylsulfonamido nitrogen are optionally substituted. The compounds are active herbicides and some are anti-inflammatory agents and analgesic agents.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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This invention relates to new alkane-sulfonanilide derivatives of the formula: STR1 wherein R1, R2 and R8 are each hydrogen, cyano, halogen, lower alkyl, halo (lower) alkyl, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl or lower alkoxy, R3 is lower alkyl, R4 is acyl, cyano, carboxy, hydroxy(lower)-alkyl, mercapto, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, 5-membered unsaturated heterocyclic group which may have amino, lower alkanoylamino, lower alkylthio or lower alkylsulfonyl, phenylthio which may have nitro or amino, lower alkanoyl(lower)alkenyl or a group of the formula: STR2 wherein R6 is hydrogen, amino or lower alkyl and R7 is hydroxy, lower alkoxy, carboxy(lower)alkoxy, lower alkoxycarbonyl(lower)alkoxy, ureido or thioureido, and R5 is hydrogen, halogen, lower alkyl or lower alkanoyl, and pharmaceutically acceptable salts thereof. More particularly, it relates to alkanesulfonanilide derivatives and pharmaceutically acceptable salts thereof which have antiinflammatory activities and analgesic activities, to processes for the preparation thereof, to a pharmaceutical composition comprising the same and to a method for the treatment of inflammatory disease or pains in human being and animals”.

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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”