Silver acetate triphenylphosphine

The Garner group has developed a silver acetate/triphenylphosphine (10mol%) catalyzed one-pot three-component coupling (Scheme 2.20) of aldehydes 72, methyl acrylate (27), and dimethyl-2-aminomalonate (73,2 equiv).39 Notably, both aliphatic and aromatic aldehydes may participate in the reaction and yields up to 95% can be achieved. 

Palladium(ll) acetate, 389-392 Palladium(II) acetate-1,2-bis(diphenylphosphino)ethane, 391-392 Palladium acetate-triphenylphosphine, 392 Palladium catalysts, 392-393 Palladium(II) chloride, 393-394 Palladium(II) ehloride-eopper(I) cloride, 346 Palladium(II) chloride-silver(I) acetate, 396-397... 

The successful implementation of this strategy is shown in Scheme 4. In the central double cyclization step, the combined action of palladium(n) acetate (10 mol %), triphenylphosphine (20 mol %), and silver carbonate (2 equiv.) on trienyl iodide 16 in refluxing THF results in the formation of tricycle 20 (ca. 83 % yield). Compound 20 is the only product formed in this spectacular transformation. It is noteworthy that the stereochemical course of the initial insertion (see 17—>18) is guided by an equatorially disposed /-butyldimethylsilyl ether at C-6 in a transition state having a preferred eclipsed orientation of the C-Pd a bond and the exocyclic double bond (see 17). Insertion of the trisubstituted cycloheptene double bond into the C-Pd bond in 18 then gives a new organopal-... 

The development of methods to effect nucleophilic addition to carbon-carbon double bonds by prior activation with metal cations has been applied, at least in a preliminary way, as a method of pyrrole ring closure. The conversion of butadienes to N-substituted pyrroles can be accomplished in two stages. In acetic add, 1,4-dienes react with PdnCl2 to give tr-allyl complexes with introduction of acetate at C-4. The ir-allyl complexes then react with amines to give a l-amino-4-acetoxy-2-butene (equation 70). When the addition of the amine is carried out in the presence of a silver salt and triphenylphosphine, a pyrrole is isolated, probably by cyclization of the amino-substituted allyl-Pd complex (equation 71) (81CC59). Although this procedure is attractive in terms of the simplicity of the... 

Iodine-copper(II) acetate, 267 Iodine-mercury(II) oxide, 267-268 Iodine monochloride, 268-269 Iodine-silver carboxylates, 268 Iodine-silver nitrate, 268 lodoamination, 265-266 Iodocarbamation, 264-265 Iodocarbonates, 263 2 Iodoestradiol, 267 2-Iodoestrone, 267 Iodoiactonization, 263-264 C,-Iodomethylcephalosporins, 273 Iodonium di-svm-collidine perchlorate, 269 19-Iodononadecanic acid, 488 Iodophenylbis(triphenylphosphine)palladium, 269... 

Palladium acetate (3.68 mmol) was added to a suspension of silver carbonate (36.8 mmol), triphenylphosphine (7.36 mmol), and the Step 3 product (18.4 mmol) in 92 ml acetonitrile, then refluxed 30 minutes. The mixture was cooled, filtered through a plug of celite, and the filter cake washed with 100 ml apiece EtOAc and diethyl ether. The filtrates were washed with 100 ml brine, dried, and concentrated. The residue was purified by flash column chromatography using 150 ml diethyl ether followed by 150 ml EtOAc and the product isolated in 58% yield as an yellow solid. 

Potassium permanganate. Dimethyl sulfide-Chlorine. Dimethyl sulfoxide. Dimethyl sulfoxide-Chlorine. Dimethylsulf-oxide Sulfur trioxide. Dipyridine chro-mium(VI) oxide. Iodine. Iodine-Potassium iodide. Iodine tris(trifluoroacetate). Iodosobenzene diacetate. Isoamyl nitrite. Lead tetraacetate. Manganese dioxide. Mercuric acetate. Mercuric oxide. Osmium tetroxide—Potassium chlorate. Ozone. Periodic acid. Pertrifluoroacetic acid. Potassium ferrate. Potassium ferricyanide. Potassium nitrosodisulfonate. Ruthenium tetroxide. Selenium dioxide. Silver carbonate. Silver carbonate-Celite. Silver nitrate. Silver oxide. Silver(II) oxide. Sodium hypochlorite. Sulfur trioxide. Thalli-um(III) nitrate. Thallium sulfate. Thalli-um(III) trifluoroacetate. Triphenyl phosphite ozonide. Triphenylphosphine dibromide. Trityl fluoroborate. 

V. Braun reaction Cyanogen bromide. Phosphorus tribromide. Piperidine. Thionyl chloride. Bromination Aluminum bromide. Aluminum chloride. Boron tribromide. Bromine chloride. N-Bromocaprolactam. N-Bromosuccinimide. Bromotrichloromethane. Cupric bromide. Dibenzoyl peroxide. l,3-Dibromo-5,5-diraethylhydantoin. 1,2-Dibromotetrachloromethane. HBr-scavengers acetamide and potassium chlorate. Iodine. Iodine monobromide. Iron. Mercuric acetate. Phenyl trimethylammonium perbromide. Phosphorus trichloride. Pyridine. Pyridine perbromide. Pyridinium hydrobromide perbromide. Silver sulfate. Sodium acetate. Sodium hypobromite. Sulfur. Sulfur monochloride. Tetramethylaramonium tribromide. M-Tribromoacetophenone. Trichloromethane sulfonyl bromide. Trilluoroacetyl hypobromite. Triphenylphosphine dibromide. 

CLEAVAGE OF ETHERS Aluminum chloride. Boron tribromide. Bromine. Dimethylformamide. Methylmagnesium iodide. Triphenylphosphine dibromide. a-GLYCOLS Silver iododibenzoate KETOXIMES Chromous acetate METHYL ESTERS Lithium n-propyl mercaptide. 

Alkenylations can also be carried out the optimum conditions for 2-bromopropene with palladium acetate include the use of triphenylarsine with silver carbonate and triethylamine, but the advantages over more amenable conditions, using triphenylphosphine with potassium or cesium carbonate, are marginal. ... 

The foregoing hydrochloride when treated with silver or barium hydroxide only yields triphenylphosphine dihydroxide, (CgPIg)3P(OH)2, but if concentrated aqueous sodium hydroxide or carbonate be used, the free betaine is isolated. It separates from alcohol in tabular crystals, M.pt. 124° to 126° C., which readily dissolve in chloroform or acetic acid, and when heated i ith water give the dihydroxide. It forms a platinicliloride, consisting of long, golden-yellow needles. The decompositions mentioned above are indicated by the following equations —... 

The crystal structure of the gold(i) complex [CeF5Au(PPhs) ] has been determined. It is approximately linear with a C—Au—P bond an e of 17go 302 The chlorine in chlorobis(pentafluorophenyl)triphenylphosphine-gold(iii) may be replaced by Br, NOj, or OAc, using potassium bromide, or silver nitrite or acetate in acetone, but an excess of potassium or silver salt causes liberation of periluorobiphenyl. It is not possible to introduce iodine using KI, but the iodo-compound is available by the route ... 

During the development of the Heck reaction of vinylBhg, silver(i) (or thal-lium(i)) acetate was shown to be a useful stoichiometric additive for enhancing the selectivity in favor of the Heck-product, especially when the coupling partner is an alkenyl system. In the latter case, further improvement can be found in replacing triphenylphosphine with tri(o-tolyl)phosphine and using silver(i) acetate as the sole base. ... 

C52H46AS2CI4M02O4 2 CH4O, Tetraphenylarsonium trans-bis(Ai-acet-ato)tetrachlorodimolybdatedi) methanol solvate, 45B, 1130 C5 3H5 sAgIrN30sP2, Isobutyrato-AX N,N -methyl-p-tolyltriazenido-silver(I)-carbonylbis(triphenylphosphine)iridium(I) - isobutyric acid, 42B, 794... 

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