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Fine Chemical Synthesis book from C.H.I.P.S.

Catalysts for Fine Chemical Synthesis
Volume 3
Metal Catalysed Carbon-Carbon Bond-Forming Reactions
Edited by Stanley M. Roberts
Jianliang Xiao
John Whittall
Tom E. Pickett

Catalysts for Fine Chemical Synthesis: Vol. 3 focuses on catalysts for carbon-carbon bond formation and presents practical and detailed protocols on how to use sophisticated catalysts by the "inventors" and "developers" who created them. The combination of protocols and review commentaries helps the reader to easily and quickly understand and use the new high-tech catalysts.

Contents

  1. Considerations of Industrial Fine Chemical Synthesis
    • Introduction
    • Types of processes – flow charts
    • Costs associated with use of catalysts

  2. Alkylation and Allylation Adjacent to a Carbonyl Group
    • The RuH2(CO)(PPh3)3-catalysed alkylation, alkenylation and arylation of aromatic ketones via carbon-hydrogen bond cleavage
    • Catalytic, asymmetric synthesis of a,a-disubstituted amino acids using a chiral copper-salen complex as a phase transfer catalyst
    • Asymmetric phase-transfer catalysed alkylation of glycine imines using cinchona alkaloid derived quaternary ammonium salts

  3. Asymmetric Alkylation or Amination of Allylic Esters
    • Synthesis and application in palladium-catalysed asymmetric allylic substitution of enantiopure cyclic Β-iminophosphine ligands
    • (9H,9’H,10H,10’H,11H,11H’,13H,13’H,14H,14’H,15H,15’Hperfluorotricosane-12,12’-diyl)bis[(4S)-4-phenyl-2-oxazoline as a ligand for asymmetric palladium-catalysed alkylation of allylic acetates in fluorous media
    • Facile synthesis of new axially chiral diphosphine complexes for asymmetric catalysis
    • Chiral ferrocenyl-imino phosphines as ligands for palladium-catalysed enantioselective allylic alkylations

  4. Suzuki Coupling Reactions
    • Palladium-catalysed borylation and Suzuki coupling (BSC) to obtain Β-benzo[b]thienyldehydroamino acid derivatives
    • Palladium-catalysed cross-coupling reactions of 4-tosylcoumarins and arylboronic acids: synthesis of 4-arylcoumarin compounds
    • Cyclopropyl arenes, alkynes and alkenes from the in situ generation of B-cyclopropyl-9-BBN and the Suzuki-Miyaura coupling of aryl, alkynyl and alkenyl bromides
    • One-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 electrophile
    • Pd(OAc)2/2-Aryl oxazoline catalysed Suzuki coupling reactions of aryl bromides and boronic acids
    • Palladium-catalysed reactions of haloaryl phosphine oxides: modular routes to functionalised ligands
    • Bulky electron rich phosphino-amines as ligands for the Suzuki coupling reaction of aryl chlorides
    • Arylation of ketones, aryl amination and Suzuki-Miyaura cross coupling using a well-defined palladium catalyst bearing an N-heterocyclic carbene ligand

  5. Heck Coupling Reactions
    • Palladium-catalysed multiple and asymmetric arylations of vinyl ethers carrying co-ordinating nitrogen auxiliaries: synthesis of arylated ketones and aldehydes
    • Palladium-catalysed highly regioselective arylation of electron-rich olefins
    • 1-[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-dihydrofuran

  6. Sonogashira Coupling Reactions
    • Nonpolar biphasic catalysis: Suzuki- and Sonogashira coupling reactions
    • Polystyrene-supported soluble palladacycle catalyst as recyclable catalyst for Heck, Suzuki and Sonogashira reactions

  7. Cross-Coupling Reactions
    • Cross-coupling reaction of alkyl halides with Grignard reagents in the presence of 1,3-butadiene catalysed by nickel, palladium, or copper
    • Triorganoindium compounds as efficient reagents for palladium-catalysed cross-coupling reactions with aryl and vinyl electrophiles
    • Cross-coupling reactions catalysed by heterogeneous nickel-on-charcoal
    • Carbon-carbon bond formation using arylboron reagents with rhodium(I) catalysts in aqueous media

  8. Regioselective or Asymmetric 1,2-Addition to Aldehydes
    • Development of a highly regioselective metal-mediated allylation reaction in aqueous media
    • Boronic acids as aryl source for the catalysed enantioselective aryl transfer to aldehydes
    • Jacobsen’s Salen as a chiral ligand for the chromium-catalysed addition of 3-chloro-propenyl pivalate to aldehydes: a catalytic asymmetric entry to syn-alk-1-ene-3,4-diols

  9. Olefin Metathesis Reactions
    • Highly active ruthenium (pre)catalysts for metathesis reactions
    • A highly active and readily recyclable olefin metathesis catalyst
    • Stereoselective synthesis of L-733,060

  10. Cyclisation Reactions
    • Molecular sieves as promoters for the catalytic Pauson-Khand reaction
    • Palladium(II)-catalysed cyclization of alkynes with aldehydes, ketones or nitriles initiated by acetoxypalladation of alkynes
    • Rhodium(I)-catalysed intramolecular alder-ene reaction and syntheses of functionalised a-methylene-g-butyrolactones and cyclopentanones
    • Rhodium-catalysed [2 ž 2 ž 2] cyclotrimerisation in an aqueous–organic biphasic system
    • Titanocene-catalysed transannular cyclisation of epoxygermacrolides: enantiospecific synthesis of eudesmanolides

  11. Asymmetric Aldol and Michael Reactions
    • Direct catalytic asymmetric aldol reaction of a a-hydroxyketone promoted by an Et2Zn/linked-BINOL complex
    • Highly enantioselective direct aldol reaction catalysed by a novel small organic molecule
    • Direct catalytic asymmetric Michael reaction of a-hydroxyketone promoted by Et2Zn/linked-BINOL complex
    • Catalytic enantioselective Michael reaction catalysed by well-defined chiral ruthenium-amido complexes

  12. Stereoselective Hydroformylation, Carbonylation and Carboxylation Reactions
    • Ortho-diphenylphosphanylbenzoyl-(o-DPPB) directed diastereoselective hydroformylation of allylic alcohols
    • The synthesis and application of ESPHOS: A new diphosphorus ligand for the hydroformylation of vinyl acetate
    • Platinum-catalysed asymmetric hydroformylation of styrene
    • Phosphine-free dimeric palladium (II) complex for the carbonylation of aryl iodides
    • Carboxylation of pyrrole to pyrrole-2-carboxylate by cells of Bacillus megaterium in supercritical carbon dioxide

Index

See also:
Volume 1: Hydrolysis, Oxidation and Reduction
Volume 2: Catalysis by Polyoxometalates


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Catalysts for Fine Chemical Synthesis
Volume 3
Metal Catalysed Carbon-Carbon Bond-Forming Reactions
Edited by Stanley M. Roberts, Jianliang Xiao, John Whittall and Tom E. Pickett

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