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Catalysts For Fine Chemical Sy, Vol. 1 Book

Catalysts For Fine Chemical Sy, Vol. 1
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  • Catalysts For Fine Chemical Sy, Vol. 1
  • Written by author Roberts
  • Published by Wiley, John & Sons, Incorporated, September 2002
  • Catalysts are increasingly used by chemists working in fine chemical synthesis in industry and academia. Today, there exists a huge choice of high-tech catalysts, which add enormously to the repertoire of synthetic possibilities. However, catalysts are tr
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1Considerations of industrial fine chemical synthesis1
2Alkylation and allylation adjacent to a carbonyl group13
2.1The RuH[subscript 2](CO)(PPh[subscript 3])[subscript 3]-catalysed alkylation, alkenylation and arylation of aromatic ketones via carbon-hydrogen bond cleavage14
2.2Catalytic, asymmetric synthesis of [alpha],[alpha]-disubstituted amino acids using a chiral copper-salen complex as a phase transfer catalyst21
2.3Asymmetric phase-transfer catalysed alkylation of glycine imines using cinchona alkaloid derived quaternary ammonium salts27
3Asymmetric alkylation or amination of allylic esters35
3.1Synthesis and application in palladium-catalysed asymmetric allylic substitution of enantiopure cyclic [beta]-iminophosphine ligands36
3.2(9H,9'H,10H,10'H,11H,11H',13H,13'H,14H,14'H,15H,15'H -perfluorotricosane-12,12'-diyl)bis[(4s)-4-phenyl-2-oxazoline as a ligand for asymmetric palladium-catalysed alkylation of allylic acetates in fluorous media40
3.3Facile synthesis of new axially chiral diphosphine complexes for asymmetric catalysis47
3.4Chiral ferrocenyl-imino phosphines as ligands for palladium-catalysed enantioselective allylic alkylations51
4Suzuki coupling reactions59
4.1Palladium-catalysed borylation and Suzuki coupling (BSC) to obtain [beta]-benzo[b]thienyldehydroamino acid derivatives60
4.2Palladium-catalysed cross-coupling reactions of 4-tosylcoumarins and arylboronic acids : synthesis of 4-arylcoumarin compounds64
4.3Cyclopropyl arenes, alkynes and alkenes from the in situ generation of B-cyclopropyl-9-BBN and the Suzuki-Miyaura coupling of aryl, alkynyl and alkenyl bromides67
4.4One-pot synthesis of unsymmetrical 1,3-dienes through palladium-catalysed sequential borylation of a vinyl electrophile by a diboron and cross-coupling with a distinct vinyl electrophile70
4.5Pd(OAc)[subscript 2]/2-Aryl oxazoline catalysed Suzuki coupling reactions of aryl bromides and boronic acids74
4.6Palladium-catalysed reactions of haloaryl phosphine oxides : modular routes to functionalised ligands77
4.7Bulky electron rich phosphino-amines as ligands for the Suzuki coupling reaction of aryl chlorides81
4.8Arylation of ketones, aryl amination and Suzuki-Miyaura cross coupling using a well-defined palladium catalyst bearing an N-heterocyclic carbene ligand86
5Heck coupling reactions91
5.1Palladium-catalysed multiple and asymmetric arylations of vinyl ethers carrying co-ordinating nitrogen auxiliaries : synthesis of arylated ketones and aldehydes92
5.2Palladium-catalysed highly regioselective arylation of electron-rich olefins100
5.31-[4-(S)-tert-Butyl-2-oxazolin-2-yl]-2-(S)-(diphenylphosphino) ferrocene as a ligand for the palladium-catalysed intermolecular asymmetric Heck reaction of 2,3-dihydrofuran104
6Sonogashira coupling reactions113
6.1Nonpolar biphasic catalysis : Suzuki- and Sonogashira coupling reactions113
6.2Polystyrene-supported soluble palladacycle catalyst as recyclable catalyst for Heck, Suzuki and Sonogashira reactions116
7Cross-coupling reactions127
7.1Cross-coupling reaction of alkyl halides with Grignard reagents in the presence of 1,3-butadiene catalysed by nickel, palladium, or copper128
7.2Triorganoindium compounds as efficient reagents for palladium-catalysed cross-coupling reactions with aryl and vinyl electrophiles133
7.3Cross-coupling reactions catalysed by heterogeneous nickel-on-charcoal138
7.4Carbon-carbon bond formation using arylboron reagents with rhodium(I) catalysts in aqueous media147
8Regioselective or asymmetric 1,2-addition to aldehydes155
8.1Development of a highly regioselective metal-mediated allylation reaction in aqueous media156
8.2Boronic acids as aryl source for the catalysed enantioselective aryl transfer to aldehydes161
8.3Jacobsen's Salen as a chiral ligand for the chromium-catalysed addition of 3-chloro-propenyl pivalate to aldehydes : a catalytic asymmetric entry to syn-akl-1-ene-3,4-diols164
9Olefin metathesis reactions169
9.1Highly active ruthenium (pre)catalysts for metathesis reactions169
9.2A highly active and readily recyclable olefin metathesis catalyst174
9.3Stereoselective synthesis of L-733,060178
10Cyclisation reactions181
10.1Molecular sieves as promoters for the catalytic Pauson-Khand reaction182
10.2Palladium(II)-catalysed cyclization of alkynes with aldehydes, ketones or nitriles initiated by acetoxypalladation of alkynes185
10.3Rhodium(I)-catalysed intramolecular alder-ene reaction and syntheses of functionalised [alpha]-methylene-[gamma]-butyrolactones and cyclopentanones190
10.4Rhodium-catalysed [2+2+2] cyclotrimerisation in an aqueous-organic biphasic system193
10.5Titanocene-catalysed transannular cyclisation of epoxygerm-acrolides : enantiospecific synthesis of eudesmanolides196
11Asymmetric aldol and Michael reactions201
11.1Direct catalytic asymmetric aldol reaction of a [alpha]-hydroxyketone promoted by an Et[subscript 2]Zn/linked-BINOL complex202
11.2Highly enantioselective direct aldol reaction catalysed by a novel small organic molecule208
11.3Direct catalytic asymmetric Michael reaction of [alpha]-hydroxyketone promoted by Et[subscript 2]Zn/linked-BINOL complex210
11.4Catalytic enantioselective Michael reaction catalysed by well-defined chiral ruthenium-amido complexes216
12Stereoselective hydroformylation, carbonylation and carboxylation reactions225
12.1Ortho-diphenylphosphanylbenzoyl-(o-DPPB) directed diastereoselective hydroformylation of allylic alcohols226
12.2The synthesis and application of ESPHOS : a new diphosphorus ligand for the hydroformylation of vinyl acetate230
12.3Platinum-catalysed asymmetric hydroformylation of styrene238
12.4Phosphine-free dimeric palladium (II) complex for the carbonylation of aryl iodides244
12.5Carboxylation of pyrrole to pyrrole-2-carboxylate by cells of Bacillus megaterium in supercritical carbon dioxide247


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