Catalysts for Fine Chemical Synthesis, Catalysts for Carbon-Carbon Bond Formation / Edition 1

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Overview

In this book the reader will find worked examples of a selection of Carbon-Carbon bond forming reactions including the asymmetric alkylation of aldehydes and ketones, the Michael and Pauson-Khand reactions, aldol protocols as well as hydroformylation and carboxylation. In addition to these well-established transformations, examples of relatively new methodologies are described, for example catalysts for olefin metathesis in organic synthesis are well represented. Furthermore in the light of the popularity of palladium-catalysed coupling reactions, some of the important Heck, Suzuki and Sonogashira catalysts are described in detail and their uses exemplified.

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Editorial Reviews

From the Publisher
"This reference provides detailed information for the preparation and use of relevant catalysts for the formation of carbon-carbon bonds." (Journal of the American Chemical Society, September 14, 2005)
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Product Details

Table of Contents

Series Preface.

Preface to Volume 3.

Abbreviations.

List of Chemical Names Used.

1 Considerations of Industrial Fine Chemical Synthesis(Mark W. Hooper).

1.1 Introduction

1.2 Types of processes – flow charts.

1.3 Costs associated with use of catalysts.

2 Alkylation and Allylation Adjacent to a CarbonylGroup.

2.1 TheRuH2(CO)(PPh3)3-catalysedalkylation, alkenylation and arylation of aromatic ketones viacarbon-hydrogen bond cleavage (Fumitoshi Kakiuchi, Satoshi Ueno andNaoto Chatani).

2.2 Catalytic, asymmetric synthesis of a,a-disubstituted aminoacids using a chiral copper-salen complex as a phase transfercatalyst (Michael North and Jose A. Fuentes).

2.3 Asymmetric phase-transfer catalysed alkylation of glycineimines using cinchona alkaloid derived quaternary ammonium salts(Barry Lygo and Benjamin I. Andrews).

3 Asymmetric Alkylation or Amination of AllylicEsters.

3.1 Synthesis and application in palladium-catalysed asymmetricallylic substitution of enantiopure cyclicΒ-iminophosphine ligands (Maria Zablocka, Marek Koprowski,Jean-Pierre Majoral, Mathieu Achard and GérardBuono).

3.2(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-oxazolineas a ligand for asymmetric palladium-catalysed alkylation ofallylic acetates in fluorous media (JérômeBayardon and Denis Sinou).

3.3 Facile synthesis of new axially chiral diphosphine complexesfor asymmetric catalysis (Matthias Lotz, Gernot Kramer, Katja Tappeand Paul Knochel).

3.4 Chiral ferrocenyl-imino phosphines as ligands forpalladium-catalysed enantioselective allylic alkylations (PierluigiBarbaro, Claudio Bianchini, Giuliano Giambastiani and AntonioTogni).

4 Suzuki Coupling Reactions.

4.1 Palladium-catalysed borylation and Suzuki coupling (BSC) toobtain Β-benzo[b]thienyldehydroamino acid derivatives (AnaS. Abreu, Paula M. T. Ferreira and Maria-João R. P.Queiroz).

4.2 Palladium-catalysed cross-coupling reactions of4-tosylcoumarins and arylboronic acids: synthesis of 4-arylcoumarincompounds (Jie Wu, Lisha Wang, Reza Fathi and Zhen Yang).

4.3 Cyclopropyl arenes, alkynes and alkenes from the insitu generation of B-cyclopropyl-9-BBN and the Suzuki-Miyauracoupling of aryl, alkynyl and alkenyl bromides (Ramon E. Huertasand John A. Soderquist).

4.4 One-pot synthesis of unsymmetrical 1,3-dienes throughpalladium-catalysed sequential borylation of a vinyl electrophileby a diboron and cross-coupling with a distinct vinyl electrophile(Tatsuo Ishiyama and Norio Miyaura).

4.5 Pd(OAc)2/2-Aryl oxazoline catalysedSuzuki coupling reactions of aryl bromides and boronic acids (BinTao and David W. Boykin).

4.6 Palladium-catalysed reactions of haloaryl phosphine oxides:modular routes to functionalised ligands (Colin Baillie, Lijin Xuand Jianliang Xiao).

4.7 Bulky electron rich phosphino-amines as ligands for theSuzuki coupling reaction of aryl chlorides (Matthew L. Clarke andJ. Derek Woollins).

4.8 Arylation of ketones, aryl amination and Suzuki-Miyauracross coupling using a well-defined palladium catalyst bearing anN-heterocyclic carbene ligand (Nicholas Marion, Oscar Navarro, RoyA. Kelly III and Steven P. Nolan).

5 Heck Coupling Reactions.

5.1 Palladium-catalysed multiple and asymmetric arylations ofvinyl ethers carrying co-ordinating nitrogen auxiliaries: synthesisof arylated ketones and aldehydes (Peter Nilsson and MatsLarhed).

5.2 Palladium-catalysed highly regioselective arylation ofelectron-rich olefins (Lijin Xu, Jun Mo and Jianliang Xiao).

5.31-[4-(S)-tert-Butyl-2-oxazolin-2-yl]-2-(S)-(diphenylphosphino)ferrocene as a ligand for the palladium-catalysed intermolecularasymmetric Heck reaction of 2,3-dihydrofuran (Tim G. Kilroy, YvonneM. Malone and Patrick J. Guiry).

6 Sonogashira Coupling Reactions.

6.1 Nonpolar biphasic catalysis: Suzuki- and Sonogashiracoupling reactions (Anupama Datta and Herbert Plenio)

6.2 Polystyrene-supported soluble palladacycle catalyst asrecyclable catalyst for Heck, Suzuki and Sonogashira reactions(Chih-An Lin and Fen-Tair Luo).

7 Cross-Coupling Reactions.

7.1 Cross-coupling reaction of alkyl halides with Grignardreagents in the presence of 1,3-butadiene catalysed by nickel,palladium, or copper (Jun Terao and Nobuaki Kambe).

7.2 Triorganoindium compounds as efficient reagents forpalladium-catalysed cross-coupling reactions with aryl and vinylelectrophiles (Luis A. Sarandeses and JoséPérez Sestelo).

7.3 Cross-coupling reactions catalysed by heterogeneousnickel-on-charcoal (Bryan A. Frieman and Bruce H. Lipshutz).

7.4 Carbon-carbon bond formation using arylboron reagents withrhodium(I) catalysts in aqueous media (John Mancuso, MasahiroYoshida and Mark Lautens).

8 Regioselective or Asymmetric 1,2-Addition toAldehydes.

8.1 Development of a highly regioselective metal-mediatedallylation reaction in aqueous media (Kui-Thong Tan, Shu-Sin Chng,Hin-Soon Cheng and Teck-Peng Loh).

8.2 Boronic acids as aryl source for the catalysedenantioselective aryl transfer to aldehydes (Jens Rudolph andCarsten Bolm).

8.3 Jacobsen’s Salen as a chiral ligand for thechromium-catalysed addition of 3-chloro-propenyl pivalate toaldehydes: a catalytic asymmetric entry to syn-alk-1-ene-3,4-diols(Marco Lombardo, Sebastiano Licciulli, Stefano Morganti and ClaudioTrombini).

9 Olefin Metathesis Reactions.

9.1 Highly active ruthenium (pre)catalysts for metathesisreactions (Syuzanna Harutyunyan, Anna Michrowska and KarolGrela).

9.2 A highly active and readily recyclable olefin metathesiscatalyst (Stephen J. Connon, Aideen M. Dunne and SiegfriedBlechert).

9.3 Stereoselective synthesis of L-733,060 (G. Bhaskar and B.Venkateswara Rao)

10 Cyclisation Reactions.

10.1 Molecular sieves as promoters for the catalyticPauson-Khand reaction (Jaime Blanco-Urgoiti, GemaDom&ıacute;nguez and JavierPérez-Castells).

10.2 Palladium(II)-catalysed cyclization of alkynes withaldehydes, ketones or nitriles initiated by acetoxypalladation ofalkynes (Ligang Zhao and Xiyan Lu).

10.3 Rhodium(I)-catalysed intramolecular alder-ene reaction andsyntheses of functionalised a-methylene-g-butyrolactones andcyclopentanones (Minsheng He, Aiwen Lei and Xumu Zhang).

10.4 Rhodium-catalysed [2 þ 2 þ 2] cyclotrimerisationin an aqueous–organic biphasic system (Hiroshi Shinokubo andKoichiro Oshima).

10.5 Titanocene-catalysed transannular cyclisation ofepoxygermacrolides: enantiospecific synthesis of eudesmanolides(Antonio Rosales, Juan M. Cuerva and J. Enrique Oltra).

11 Asymmetric Aldol and Michael Reactions.

11.1 Direct catalytic asymmetric aldol reaction of aa-hydroxyketone promoted by an Et2Zn/linked-BINOL complex(Masakatsu Shibasaki, Shigeki Matsunaga and Naoya Kumagai).

11.2 Highly enantioselective direct aldol reaction catalysed bya novel small organic molecule (Zhuo Tang, Liu-Zhu Gong, Ai-Qiao Miand Yao-Zhong Jiang).

11.3 Direct catalytic asymmetric Michael reaction ofa-hydroxyketone promoted by Et2Zn/linked-BINOL complex (MasakatsuShibasaki, Shigeki Matsunaga and Naoya Kumagai).

11.4 Catalytic enantioselective Michael reaction catalysed bywell-defined chiral ruthenium-amido complexes (Masahito Watanabe,Kunihiko Murata, and Takao Ikariya).

12 Stereoselective Hydroformylation, Carbonylation andCarboxylation Reactions.

12.1 Ortho-diphenylphosphanylbenzoyl-(o-DPPB) directeddiastereoselective hydroformylation of allylic alcohols (BernhardBreit).

12.2 The synthesis and application of ESPHOS: A new diphosphorusligand for the hydroformylation of vinyl acetate (Martin Wills andSimon W. Breeden).

12.3 Platinum-catalysed asymmetric hydroformylation of styrene(Submitted by Stefánia Cserépi-Szücsand József Bakos).

12.4 Phosphine-free dimeric palladium (II) complex for thecarbonylation of aryl iodides (C. Ramesh, Y. Kubota and Y.Sugi).

12.5 Carboxylation of pyrrole to pyrrole-2-carboxylate by cellsof Bacillus megaterium in supercritical carbon dioxide (TomokoMatsuda, Tadao Harada, Toru Nagasawa and Kaoru Nakamura).

Index.

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