Copper salts amides

The above-described structures are the main representatives of the family of nitrogen ligands, which cover a wide spectrum of activity and efficiency for catalytic C - C bond formations. To a lesser extent, amines or imines, associated with copper salts, and metalloporphyrins led to good catalysts for cyclo-propanation. Interestingly, sulfinylimine ligands, with the chirality provided solely by the sulfoxide moieties, have been also used as copper-chelates for the asymmetric Diels-Alder reaction. Amide derivatives (or pyridylamides) also proved their efficiency for the Tsuji-Trost reaction. 

Copper salts, cupric or cuprous also will catalyze the carbonylation of amines. Piperidine, for example, gives a urea derivative with carbon monoxide, and it, too, is probably a metal amide—carbon monoxide insertion reaction. 

Ger), C6Hs.CO.NH.OH or CgH8.C(OH) N.OHj mw 137.13, N 10.21% rhom ifts(exists in two isometric types), mp 124-6° 131-2° (values reported by various investigators) exp or rapid heating v sol in ale si sol in w or eth insol in benz. Can t>c prepd by the action of hydroxyl s id in c on the esters, chloride or amide of benzoic acid and by otu methous(Ref 1). It forms numerous addn compds and salts, such as the Copper salt, Cu-(C7H6N02)2, It blue cryst which expi mildly on heating(Ref 2)... 

Copper Cyan amide. See under Cyanamide and its Salts. 

Mercurioferrocenes (290) and (291) are separable by Soxhlet extraction and these may be used to prepare bromoferrocene or dibromoferrocene or the iodo analogs. Alternatively, these halogenated ferrocenes are prepared from the ferrocene boronic acids or from anions (322) or (323). Bromoferrocene is the starting material for cyanoferrocene, azidoferrocene, or aminoferrocenes, generally in the presence of a copper salt. Amtnoferrocene can be acylated to produce an amide, or converted to isocyanoferrocene by a formylation/dehydration sequence (Scheme 96). The 1,T-diisocyanoferrocene is available from the bis(acyl)azide, itself derived from ferrocene dicarboxylic acid. ... 

Reductive desulfurization of the dithioketals 5.14 and 5.15 is performed under the same conditions as for thioethers [G02] LAH in the presence of copper salts or borohydrides in the presence of nickel salts (Figure 5.8). The deoxygenation of tertiary amine-oxides such as 5.16 and 5.17 can be performed with borohydride exchange resin-copper sulfate in methanol at room temperature or under reflux. This reaction tolerates other functional groups such as carbon-carbon double bonds, chlorides, epoxides, esters, amides, nitriles, sulfoxides, and sulfones [SA4] (Figure 5.8). 

Fusaric acid (5- i-butylpyridine-2-carboxylic acid) [536-69-6] M 179.2, m 96-98 , 98 , 98-100°, 101-103°, pKi 5.7, pK2 6.16 (80% aqueous methoxyethanol). Dissolve it in CHCI3, diy (Na2S04), filter, evaporate and recrystallise the residue from 50 parts of pet ether (b 40-60°), CHCl3/pet ether or EtOAc, then sublime it in vacuo. The amide crystallises from MeOH with in 128.2-129.0°. The copper salt forms bluish violet crystals from H2O and has m 258-259°. [Hardegger Nikles Helv Chim Acta 3 9 505 1956, Schreiber Adam Chem Ber 93 1848 1960, NMR and MS Tschesche Fiihrer Chem Ber 111 3500 1978, Beilstein 22 III/IV 764, 22/2 V 384.]... 

Peptide synthesis [1, 1246, before references]. In the presence of triphenylphosphine, copper salts of carboxylic acids undergo condensation with sulfen-amides 33... 

TARTARIC ACID, COPPER SALT (815-82-7) C4H4CuOg Contact with acetylene forms unstable and explosive acetylides. Contact with nitromethane forms explosive compounds. Aqueous solution is acidic. Incompatible with bases, amines, amides, and inorganic hydroxides. 

Arylations. Arylation of malonic esters is achieved in good yields. The less electron-rich aryl group is transferred from unsymmetrical iodonium salts. A-Arylation of amines, amides, and lactams is under catalysis by Cul, whereas pyrimidinones undergo A-arylation using t-BuOK as base (no copper salt).- ... 

Oxidative cleavage of acid hydrazides. Oxygen activated by copper salts converts acid hydrazides into carboxylic acids (equation I), esters (equation II), or amides (equation III). All reactions occur at 20° without oxidation of other sensitive groups. ... 

Oxidations employing copper salts are among the newer methods introduced and have proven to be quite usefiil. For example, CuBr2/DBU/HMTA was used to convert oxazolines to 2-aIkyl(aryl)-4-oxazolecarboxyIic acid esters or amides (Scheme Banish and co-workers" proposed that the mechanism of... 

By using the Liebeskind catalyst copper(I) thiophene-2-carboxylate (copper salt of L8), the coupling reaction of vinyl iodides and amides proceeded smoothly to give the corresponding enamides (Table 9.7, entry 1) [37]. CuI/DMEDA (Lll) was another efficient catalytic system for the coupling of vinyl halides with amides (entry 2) [38]. 

Allylic silanes can be converted into allylic tosylamides by the reaction with PhINTs in the presence of copper salts. In particular, the copper(I)-catalyzed enantioselective amidation of the chiral ( )-crotylsilanes 659 (Scheme 3.263) has been used in the asymmetric synthesis of ( )-olefin dipeptide isosteres [806]. 

Coordination of nitrile to metal directly through the nitrogen or through some other proximal atom activates the carbon toward nucleophilic attack by water and other nucleophiles. The products are commonly amides. The metal-mediated reactions of dicyanodiamide (19) have been further investigated in the presence of nickel or copper salts (19) reacts with alcohols to yield (20). 

Linoleic acid. See Linoleic acid Linoleic acid amide. See Linoleamide Linoleic acid, copper salt. See Copper linoleate Linoleic acid diethanolamide. See Linoleamide DEA... 

Reactions with aikynes may aiso result in the formation of cyclized products. Thus a ruthenium-catalysed reaction with aromatic amides has been used to give isoquinoline derivatives. On the basis of values of the kinetic isotope effect, A h/ d> proposed that the rate-determining step is a concerted acetate-assisted metalation-deprotonation process to yield the intermediate (30), followed by aikyne insertion and ring closure. The reaction of arylketones with alkynes may yield indenols when catalysed by rhodium cyclopentadienyl in the presence of silver and copper salts. The reaction proceeds regioselectively, so that reaction of acetophenone with 1-phenyl-1-propene... 

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