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Catalysts for Fine Chemical Synthesis
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Edited by Stanley M. Roberts and Jianliang Xiao University of Liverpool, UK John Whittall and Tom E. Pickett The Heath, Runcorn Stylacats Ltd, UK Contents Series Preface . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xvii Preface to Volume 3 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xix Abbreviations . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xxi List of Chemical Names Used . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xxiii 1 Considerations of Industrial Fine Chemical Synthesis 1 Mark W. Hooper . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 1.1 Introduction 1.2 Types of processes – flow charts . . . . . . . . . . . . . . . . . . . . . . . . 2 1.3 Costs associated with use of catalysts . . . . . . . . . . . . . . . . . . . . 3 2 Alkylation and Allylation Adjacent to a Carbonyl Group 13 2.1 The RuH2(CO)(PPh3)3-catalysed alkylation,alkenylation and arylation of aromatic ketones via carbon-hydrogen bond cleavage Fumitoshi Kakiuchi, Satoshi Ueno and Naoto Chatani . . . . . . . . . 14 2.2 Catalytic, asymmetric synthesis of a,a-disubstituted amino acids using a chiral copper-salen complex as a phase transfer catalyst Michael North and Jose A. Fuentes . . . . . . . . . . . . . . . . . . . . . 21 2.3 Asymmetric phase-transfer catalysed alkylation of glycine imines using cinchona alkaloid derived quaternary ammonium salts Barry Lygo and Benjamin I. Andrews . . . . . . . . . . . . . . . . . . . 27 3 Asymmetric Alkylation or Amination of Allylic Esters 35 3.1 Synthesis and application in palladium-catalysed asymmetric allylic substitution of enantiopure cyclic b-iminophosphine ligands， Maria Zablocka, Marek Koprowski, Jean-Pierre Majoral,Mathieu Achard and Ge′rard Buono . . . . . . . . . . . . . . . . . . . . . 36 3.2(9H,90H,10H,100H,11H,11H0,13H,130H,14H,140H,15H,150Hperfluorotricosane-12,120-diyl)bis[(4S)-4-phenyl-2-oxazoline as a ligand for asymmetric palladium catalysed alkylation of allylic acetates in fluorous media Je′roˆme Bayardon and Denis Sinou . . . . . . . . . . . . . . . . . . . . . 40 3.3 Facile synthesis of new axially chiral diphosphine complexes for asymmetric catalysis Matthias Lotz, Gernot Kramer, Katja Tappe and Paul Knochel 47 3.4 Chiral ferrocenyl-imino phosphines as ligands for palladium-catalysed enantioselective allylic alkylations Pierluigi Barbaro, Claudio Bianchini, Giuliano Giambastiani and Antonio Togni . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51 4 Suzuki Coupling Reactions 59 4.1 Palladium-catalysed borylation and Suzuki coupling (BSC) to obtain b-benzothienyldehydroamino acid derivatives Ana S. Abreu, Paula M. T. Ferreira and Maria-Joa˜o R. P. Queiroz 60 4.2 Palladium-catalysed cross-coupling reactions of 4-tosylcoumarins and arylboronic acids: synthesis of 4-arylcoumarin compounds Jie Wu, Lisha Wang, Reza Fathi and Zhen Yang . . . . . . . . . . . . 64 4.3 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 Ramon E. Huertas and John A. Soderquist . . . . . . . . . . . . . . . . 67 4.4 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 Tatsuo Ishiyama and Norio Miyaura . . . . . . . . . . . . . . . . . . . . 70 4.5 Pd(OAc)2/2-Aryl oxazoline catalysed Suzuki coupling reactions of aryl bromides and boronic acids Bin Tao and David W. Boykin . . . . . . . . . . . . . . . . . . . . . . . . . 74 4.6 Palladium-catalysed reactions of haloaryl phosphine oxides: modular routes to functionalised ligands Colin Baillie, Lijin Xu and Jianliang Xiao . . . . . . . . . . . . . . . . 77 4.7 Bulky electron rich phosphino-amines as ligands for the Suzuki coupling reaction of aryl chlorides Matthew L. Clarke and J. Derek Woollins . . . . . . . . . . . . . . . . 81 4.8 Arylation of ketones, aryl amination and Suzuki-Miyaura cross coupling using a well-defined palladium catalyst bearing an N-heterocyclic carbene ligand Nicholas Marion, Oscar Navarro, Roy A. Kelly III and Steven P. Nolan . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 86 5 Heck Coupling Reactions 91 5.1 Palladium-catalysed multiple and asymmetric arylations of vinyl ethers carrying co-ordinating nitrogen auxiliaries: synthesis of arylated ketones and aldehydes Peter Nilsson and Mats Larhed . . . . . . . . . . . . . . . . . . . . . . . . 92 5.2 Palladium-catalysed highly regioselective arylation of electron-rich olefins Lijin Xu, Jun Mo and Jianliang Xiao . . . . . . . . . . . . . . . . . . . . 100 5.3 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 Tim G. Kilroy, Yvonne M. Malone and Patrick J. Guiry . . . . . . . 104 CONTENTS ix 6 Sonogashira Coupling Reactions 113 6.1 Nonpolar biphasic catalysis: Suzuki- and Sonogashira coupling reactions Anupama Datta and Herbert Plenio . . . . . . . . . . . . . . . . . . . 113 6.2 Polystyrene-supported soluble palladacycle catalyst as recyclable catalyst for Heck, Suzuki and Sonogashira reactions Chih-An Lin and Fen-Tair Luo . . . . . . . . . . . . . . . . . . . . . . . 116 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 125 Reference . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 125 7 Cross-Coupling Reactions 127 7.1 Cross-coupling reaction of alkyl halides with Grignard reagents in the presence of 1,3-butadiene catalysed by nickel, palladium, or copper Jun Terao and Nobuaki Kambe . . . . . . . . . . . . . . . . . . . . . . . 128 7.2 Triorganoindium compounds as efficient reagents for palladium-catalysed cross-coupling reactions with aryl and vinyl electrophiles Luis A. Sarandeses and Jose′ Pe′rez Sestelo . . . . . . . . . . . . . . . 133 7.3 Cross-coupling reactions catalysed by heterogeneous nickel-on-charcoal Bryan A. Frieman and Bruce H. Lipshutz . . . . . . . . . . . . . . . . 138 7.4 Carbon-carbon bond formation using arylboron reagents with rhodium(I) catalysts in aqueous media John Mancuso, Masahiro Yoshida and Mark Lautens . . . . . . . 147 8 Regioselective or Asymmetric 1,2-Addition to Aldehydes 155 8.1 Development of a highly regioselective metal-mediated allylation reaction in aqueous media Kui-Thong Tan, Shu-Sin Chng, Hin-Soon Cheng and Teck-Peng Loh 156 8.2 Boronic acids as aryl source for the catalysed enantioselective aryl transfer to aldehydes Jens Rudolph and Carsten Bolm . . . . . . . . . . . . . . . . . . . . . . 161 8.3 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 Marco Lombardo, Sebastiano Licciulli, Stefano Morganti and Claudio Trombini . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 164 9 Olefin Metathesis Reactions 169 9.1 Highly active ruthenium (pre)catalysts for metathesis reactions Syuzanna Harutyunyan, Anna Michrowska and Karol Grela . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 169 9.2 A highly active and readily recyclable olefin metathesis catalyst Stephen J. Connon, Aideen M. Dunne and Siegfried Blechert 174 9.3 Stereoselective synthesis of L-733,060 G. Bhaskar and B. Venkateswara Rao . . . . . . . . . . . . . . . . . . 178 10 Cyclisation Reactions 181 10.1 Molecular sieves as promoters for the catalytic Pauson-Khand reaction Jaime Blanco-Urgoiti, Gema Domı′nguez and Javier Pe′rez-Castells . . . . . . . . . . . . . . . . . . . . . . . . . . 182 10.2 Palladium(II)-catalysed cyclization of alkynes with aldehydes, ketones or nitriles initiated by acetoxypalladation of alkynes Ligang Zhao and Xiyan Lu . . . . . . . . . . . . . . . . . . . . . . . . . 185 10.3 Rhodium(I)-catalysed intramolecular alder-ene reaction and syntheses of functionalised a-methylene-g-butyrolactones and cyclopentanones Minsheng He, Aiwen Lei and Xumu Zhang . . . . . . . . . . . . . . 190 10.4 Rhodium-catalysed [2 t 2 t 2] cyclotrimerisation in an aqueous–organic biphasic system Hiroshi Shinokubo and Koichiro Oshima . . . . . . . . . . . . . . . 193 10.5 Titanocene-catalysed transannular cyclisation of epoxygermacrolides: enantiospecific synthesis of eudesmanolides Antonio Rosales, Juan M. Cuerva and J. Enrique Oltra . . . . . 196 11 Asymmetric Aldol and Michael Reactions 201 11.1 Direct catalytic asymmetric aldol reaction of a a-hydroxyketone promoted by an Et2Zn/linked-BINOL complex Masakatsu Shibasaki, Shigeki Matsunaga and Naoya Kumagai 202 11.2 Highly enantioselective direct aldol reaction catalysed by a novel small organic molecule Zhuo Tang, Liu-Zhu Gong, Ai-Qiao Mi and Yao-Zhong Jiang 208 11.3 Direct catalytic asymmetric Michael reaction of a-hydroxyketone promoted by Et2Zn/linked-BINOL complex Masakatsu Shibasaki, Shigeki Matsunaga and Naoya Kumagai 210 11.4 Catalytic enantioselective Michael reaction catalysed by well-defined chiral ruthenium-amido complexes Masahito Watanabe, Kunihiko Murata, and Takao Ikariya . . . 216 12 Stereoselective Hydroformylation, Carbonylation and Carboxylation Reactions 225 12.1 Ortho-diphenylphosphanylbenzoyl-(o-DPPB) directed diastereoselective hydroformylation of allylic alcohols Bernhard Breit . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 226 12.2 The synthesis and application of ESPHOS: A new diphosphorus ligand for the hydroformylation of vinyl acetate Martin Wills and Simon W. Breeden . . . . . . . . . . . . . . . . . . . 230 12.3 Platinum-catalysed asymmetric hydroformylation of styrene Submitted by Stefa′nia Csere′pi-Szu¨cs and Jo′zsef Bakos . . . . . . 238 12.4 Phosphine-free dimeric palladium (II) complex for the carbonylation of aryl iodides C. Ramesh, Y. Kubota and Y. Sugi . . . . . . . . . . . . . . . . . . . . 244 12.5 Carboxylation of pyrrole to pyrrole-2-carboxylate by cells of Bacillus megaterium in supercritical carbon dioxide Tomoko Matsuda, Tadao Harada, Toru Nagasawa and Kaoru Nakamura . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 247 [ 来自小组 狼族传说 ] [ Last edited by jiangyun2 on 2013-9-19 at 18:44 ] |
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