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[资源] Catalysts for Fine Chemical Synthesis

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

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