Palladium diacetate

Soderberg and coworkers have developed a palladium-phosphine-catalyzed reductive iV-het-eroannuladon of 2-nitrostyrenes forming indoles in good yields For example, reaction of 6-bromo-2-nitrostyrene with carbon monoxide in the presence of a catalytic amount of palladium diacetate (6 mol% and triphenylphosphine 124 mol% in acetonitrile at 30 gives 4-bromoindole in 86% yield fEq 10 62 Several functional groups, such as esters, ethers, bromides, tnflates, and additional nitro groups, have been shown to be compatible with the reaction conditions... 

Although not strictly related to the title of this section, the methyl-de-diazoniation of arenediazonium salts using tetramethylstannane, catalyzed by palladium diacetate, may also be mentioned here (Kikukawa et al., 1983). 

Diastereomerically pure (2W,5.V)-l,3-diaza-2-(2-methylphenyl)-3-phenyl-2-phosphabicyclo[3.3.0]octane (.S )-202] was formed in the thermal reaction of (S)-2-(anilinomethyl)pyrrolidines (197a) with o-TolP(NMe2)2 and isolated in 27% yield after recrystallization (Scheme 56) [87], Its cyclopalladation with palladium diacetate followed by anion metathesis gave dimer (5,5)-203 (Scheme 56) [87],... 

Similar cross-coupling reaction of another derivative of the same ring system 141 with dihydrofuran has also been described. In this case, palladium diacetate, tributylamine, triphenylphosphine, and tetrabutylammonium chloride were used to afford the product 142 in high yield (70%) <1995NN105>. 

To prepare more hydrophobic starches for specific applications, the partial substitution of starch with acetate, hydroxypropyl, alkylsiliconate or fatty-acid ester groups has been described in the literature. A new route, however, consists of grafting octadienyl chains by butadiene telomerization (Scheme 3.9) [79, 82, 83], The reaction was catalyzed by hydrosoluble palladium-catalytic systems prepared from palladium diacetate and trisodium tris(m-sulfonatophenyl)phosphine (TPPTS). 

A mixture of epoxides 483 obtained on oxidation of 482 with dimethyldioxirane, when exposed to ferric chloride provided, as the kinetically controlled product, the a-aldehyde 484, which without purification was reduced to the a-alcohol 485. The exclusive formation of 484 is believed to occur via the benzyl cation 486, generated by Lewis-acid opening of the oxirane ring, suffering a stereospecific kinetic 1,2-hydride shift The amino alcohol 487 obtained after sequential removal of O-benzyl and N-tosyl groups from 485, on treatment with triphenylphosphine and iodine in the presence of imidazole furnished the tetracyclic base 488, which was oxidised to the ketone 489. Trapping of the kinetically generated enolate of 489 as the silylether, followed by palladium diacetate oxidation yielded the enone 490. The derived... 

Amongst some specific reactions used in regioselective syntheses, we note the cyclometallation processes [Sec. 2.2.5.1, reaction (2.8) Sec. 3.1.1.2, reactions (3.40)-(3.44) Sec. 3.3.2.3, reactions (3.226)-(3.228)]. In this respect, we note that C,N-donor ligands form, depending on the nature of Lewis acids, two types of complexes. In the case of immediate interaction (4.35) of azomethines 859 with titanium or tin tetrachlorides (MC14), the molecular complexes with M—N bond 860 [101] were obtained (route A), while the cyclometallation reaction with the use of palladium diacetate leads to binuclear chelates 861, in which the Pd — N, C metal-cycles are formed (4.35) [11,114-116] ... 

Scheme 2 shows the mechanism generally accepted for the catalytic arylation of olefins with aryl iodides in the presence of a tertiary phosphine-coordinated palladium catalyst and a base (4). Oxidative addition of aryl iodide (Arl) to a Pd(0) species (A), which is most commonly generated from palladium diacetate and a tertiary phosphine ligand, forms an arylpalladium iodide complex (B). Coordination of olefin on B followed by insertion of the coordinated olefin into the Pd-Ar bond forms a a-alkylpalladium species (C), which undergoes p-hydrogen elimination reaction to give the arylation... 

Palladium diacetate catalyses the reaction of diazomethane with a(3-unsaturated ketones to give cyclopropyl ketones in high yields. Steroidal examples include formation of the products (89) and (90) from the corresponding enones.106... 

Pd(C5Ph5- / )]2( <-C2Ph2), is prepared in moderate yield from the novel acetylene-cleavage reaction between palladium diacetate and diphenylacetylene in methanol. 

Materials. Palladium diacetate, l,2-dicyanobenzene(+98%), l,2-phenylenediamine(98%), salicylaldehyde and ferrocene (+98%) were purchased from Aldrich and used as received. A sample of NaY with a Si/Al ratio of 3.7 was purchased from Ajka Aluminum Ltd. 

The quatemisation was carried by reacting the organofimctionalised silica (typically 10 g, <20 mmol aryl groups) with triphenylphosphine (lOO mmol) in xylene containing palladium diacetate (0.2 mmol) at 140°C (or 50 mmol nickel (II) bromide in benzonitrile at 200 C) for 16h. The isolated solids were thoroughly washed and finally dried at 60 C in vacuo for 2 h. The materials gave satisfactory element analysis, DRIFT spectra and MAS NMR data. 

Palladium Diacetate. Acetic acid palladium salt ... 

Butyl-2-iodophenol furnishes benzofurans 526 by the action of terminal alkynes 525 (R = Bu, HOCH2 or C02Et) in pyridine containing copper(I) oxide. Similarly, treatment of 6)-iodophenol 527 (X = CH) or the corresponding 3-pyridinol 527 (X = N) with a variety of terminal alkynes in the presence of piperidine, copper(I) iodide and bis(tri-phenylphosphine)palladium diacetate gives benzofurans 528 (X = CH) or furanopyridines 528 (X = N), respectively... 

A highly active palladium catalyst for Suzuki coupling reactions can be generated from palladium diacetate and 2-(di-tert-butylphosphino)biphenyl. Potassium fluoride is the preferred base for this system. The coupling of both bromides and chlorides proceeds at room temperature in excellent yields as exemplified by the preparation of 3-phenylthio-phene 46. Cross-coupling between 2-bromothiophene and diethyl(3-pyridmyl)borane gives a pyridinyl 2-substituted thiopene 47. ... 

Homocoupling. Homocoupling of heteroarenes leads to symmetrical coupling products as described for thiophenes (vide supra). The catalyst system can be generated from palladium diacetate and an amine base. 2-Bromothiazole is converted to the 2,2 -biheteroarene 129 in high yield under these conditions (Scheme 54). Similarly, A-tritylated 4-iodoimidazoles can be homocoupled to give 4,4 -bis(imidazoles). ... 

Acetic acid, oleyl ester. See Oleyl acetate Acetic acid, oxo-. See Glyoxalic acid Acetic acid palladium salt Acetic acid palladium (2+) salt. See Palladium diacetate Acetic acid pentyl ester. See Amyl acetate Acetic acid, phenyl-, butyl ester. See Butyl phenylacetate... 

Bisacetylpalladium. See Palladium diacetate Bis (acetyl-N-phenylcarbamylmethyl)-4,4 -disazo-3,3 -dichlorobiphenyl. See Diarylanilide yellow... 

Diacetatopalladium. See Palladium diacetate Diacetic ether. See Ethylacetoacetate Diacetin (INCI). See Glyceryl diacetate Diacetone. See Diacetone alcohol Diacetone acrylamide CAS 2873-97-4 EINECS/ELINCS 220-713-2 Synonyms Acrylamide, N-(1-1dimethyl-3-oxobutyl)- 4-Acrylamido-4-methyl-2-pentanone DAA Diallyl ester acetic acid N-(1,1-Dimethyl-3-oxobutyl) acrylamide N-(1,1-Dimethyl-3-oxobutyl)-2-propenamide N-(2-(2-Methyl-4-oxopentyl)) acrylamide N-(2-Methyl-4-oxo-2-pentyl) acrylamide 2-Propenamide, N-(1,1-dimethyl-3-oxobutyl)-Classification Acrylamide Empirical C9H15NO2... 

Diacetoxymercury. See Mercury acetate (ic) Diacetoxypalladium. See Palladium diacetate... 

Noah http //www.noahtech.com Ruger http //www.rugerchemical.com-. Sigma Spectrum Quality Prods. http //www.spectrumchemical.com. Technic Palladium diacetate... 

Palladous acetate. See Palladium diacetate Palladous chloride. See Palladium chloride (ous)... 

Ferric chloride hexahydrate Iron pentacarbonyl Palladium diacetate Phosphotungstic acid Vanadium pentoxide catalyst, organic synthesis Boron tribromide Boron trichloride Boron trifluoride Cobalt Mercury acetate (ic) Trimethylsilyl trifluoromethane sulfonate Zinc acetate... 

Diphenyl-sulfon-3,3 -disulfohydrazide Porofor D33 3375-31-3 Palladium diacetate... 

Ethoxyacetic acid Ethylene glycol acetate Glyceryl formal Methyl lactate Methyl-(S)-lactate C4H8O4 Erythrulose C4H8O4 Pd Palladium diacetate C4H8O4S Thiolanediol C4H8S... 

In the field of natural dienic macrocycles, formation of the Tetrin A skeleton was targeted through Pd-based macrolactonization of an alkenyl epoxide (Scheme 12) to afford the dienic 26-membered ring, with a yield of 92% in the case of a good n--acceptor ligand such as tri-Mo-propyl-phosphite, which reduces palladium diacetate to zerovalent palladium. 

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