Handbook of Palladium-Catalysed Organic Reactions

Front Cover
J. C. Fiaud, Jean-Luc Malleron, J. Y. Legros
Elsevier, Feb 18, 1997 - Science - 304 pages
This comprehensive handbook will be an indispensable research tool for chemists. Handbook of Palladium Catalysed Organic Reactions provides a synoptic description of the main types of reactions which are catalyzed by Palladium and the mechanism which causes these reactions. Each reaction is presented in graphical form and classified according to the type of transformation involved.
Other books covering the use of Palladium complexes as catalysts have been written, but the Handbook is the only to offer a synoptic view, showing the catalytic cycle of each reaction. This complete coverage provides the reader with a good understanding of the parameters involved. The tables included can be viewed from the point of view of the reagents, the product of the reaction, or the mechanism involved. The Handbook is a companion to the Database of Palladium Chemistry: Reactions andCatalytic Cycles, published on CD-ROM.
  • Begins with explicit instructions from the authors, facilitating use of the Handbook
  • Details the associated catalytic cycle for each class of reactions
  • Offers a choice of references, allowing the reader to find the closest example for solving a given problem
  • 84 types of mechanism covered, plus over 2500 references
  • Presents graphical abstracts for all reactions described, making it easy to search a type of reaction
  • Comb-bound for easy reference
  • Free demo disk included for the Database of Palladium Chemistry
  • A versatile tool for chemists in the academic community, this handbook will be an invaluable tool in the laboratory
 

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Contents

I Introduction
1
II Graphical abstracts of reaction numbers RXN
5
III Reactions catalysed by palladium complexes
23
RXN2 CrossCoupling of Organometallics with RCOX Derivatives
48
RXN3 CrossCoupling of Siloxycyclopropanes with RX and RCOX Derivatives
53
RXN4 CrossCoupling of Terminal Alkynes with RX Derivatives
55
RXN5 Intermolecular HECK Reaction
61
RXN6 Intramolecular HECK Reaction
72
RXN43 Tandem AcyloxylationCyclization of 15Dienes
198
RXN44 Tandem AcyloxychlorinationCyclization of 16Dienes
200
RXN45 14Acyloxychlorination of 13Dienes
202
RXN46 14Diacyloxylation of 13Dienes and Related Reactions
204
RXN47 Intramolecular Amination Alkoxylation or Acyloxylation of Alkynes
206
RXN48 Tandem Intramolecular Amination Alkoxylation or AcyloxylationAllylation of Alkynes and Allenes
208
RXN49 Tandem Intramolecular Amination Alkoxylation or AcyloxylationCarbonylation of Alkynes
210
RXN50 Intramolecular Amination or Alkoxylation of Alkenes
213

RXN7 Intramolecular Coupling of DiVinyl Halides
80
RXN8 Tandem HECKAnion Capture Process of Alkenes Alkynes Allenes and Dienes
82
RXN9 Tandem HECKAnion Capture Process of Norbornene and Related Compounds
86
RXN10 Tandem ArylsulfonationCyclization Process
89
RXN11 Tandem CyclizationAnion Capture Carbonylation Process of Alkenes Allenes and Alkynes
91
RXN12 Tandem CyclizationAnionCapture Process of EneVinyl EneAryl and EneAlkyl Halides
95
RXN13 Tandem CyclizationAnion Capture Carbonylation Process of YneVinyl and YneAryl Halides
99
RXN14 Hydroarylation and Hydrovinylation of Alkenes and Alkynes
102
RXN15 Reduction of Alkenes
106
RXN16 Semihydrogenation of Alkynes and 13Dienes
108
RXN17 Hydroboration Hydrogermylation Hydrosilylation and Hydrostannation of Alkynes Allenes Dienes and Enynes
110
RXN18 Hydroselenation of Alkynes
113
RXN19 14 Disilylation of Conjugated Enones
115
RXN20 Hydrocarboxylation Hydrocarboalkoxylation and Hydrocarboamination of Alkenes and Alkynes
117
RXN21 Tandem CarbonylationArylation with Alkynes
120
RXN22 12Dimetallation of Alkynes and Alkenes and Related Reactions
123
RXN23 12Dimetallation of Isonitriles
126
RXN24 12Dimetallation of Allenes or 13Dienes
128
RXN25 Coupling of Aryl Derivatives with Alkenes Involving a PdII Catalyst
131
RXN26 Homocoupling of Aryl and Vinyl Derivatives
133
RXN27 Codimerization of Alkynes
135
RXN28 Codimerization of Terminal Alkynes with Allenes
138
RXN29 Codimerization of Alkynes and Allyl Halides
140
RXN30 Cyclopropanation of Alkenes and 13Dienes by Diazomethane
143
RXN31 Rearrangement of αHydroxy Diazo Compounds
145
RXN32 Substitution Addition and Elimination on ProπAllyl Substrates
147
RXN33 33Sigmatropic Rearrangement and 13Shift on Allylic Derivatives
171
RXN34 13Diene Monoepoxide Rearrangement
175
RXN35 Ring Extension of Cyclobutane Derivatives
177
RXN36 3+2 3+4 3+6 1+2 Cycloadditions
180
RXN37 Intramolecular EneLike Reactions
184
RXN38 Cyclization of Hexatrienolate Derivatives
188
RXN39 Amination or Amidation of Alkenes
190
RXN40 Alkoxylation of Alkenes and Alkynes
192
RXN41 Acetalization of Alkenes
194
RXN42 Allylic Acyloxylation of Cycloalkenes
196
RXN51 Tandem Intramolecular Amination or AlkoxylationCarbonylation of Alkenes and Allenes
216
RXN52 Reductive Cyclization with Diynes and Enynes
220
RXN53 Cycloisomerization of Diynes and Enynes
222
RXN54 Cycloaddition of Aziridines with Carbodiimides
226
RXN55 Telomerization of 13Dienes with Nucleophiles
228
RXN56 WACKER Process
232
RXN57 Preparation of Ketones from Alcohols or Derivatives via a βHydride Elimination
235
RXN58 Preparation of αβUnsaturated Carbonyl Derivatives via a βHydride Elimination
238
RXN59 Preparation of αDiketones Derivatives via an Oxidative Rearrangement of a Propargyl Acetate
241
RXN60 Carbonylation
243
RXN61 Isomerization of Alkynes
253
RXN62 Addition of Thiols to Alkynes
256
RXN63 Preparation of Allylic Acetates from Alkynes by Tandem RedoxAddition
258
RXN64 Tandem CyclizationCapture Process of Enynes
260
RXN65 AldoILike Condensation of Enol Esters with Aldehydes
262
RXN66 Addition of Fluoroalkyl Iodides to Alkenes or Alkynes via a PdI Species
264
RXN67 Intermolecular Tandem CarbonylationCouplingCyclization Process of Aryl Halides with Terminal Alkynes
266
RXN68 Intramolecular Coupling of Aryl Halides with Arenes
268
RXN69 Tandem Intramolecular AlkoxylationVinylation of Alkenes
270
RXN70 Carbonylative 2+2 Cycloaddition
272
RXN71 Dicarboalkoxylation of Alkenes
274
RXN72 Addition of Pronucleophiles on 13Dienes or Allenes
276
RXN73 Tandem CycloisomerizationCycloaddition of Dienynes with 13Dienes via Metallodienes
279
RXN74 Acylcyanation of Terminal Alkynes
281
RXN75 14Carbochlorination
283
RXN76 Tandem ChlorinationCyclization and Tandem ChlorinationCarbonylationCyclization of 16Enynes
285
RXN77 Intramolecular Cyclocarbonylation of Alkenes
288
RXN78 Tandem CarbonylationCyclization of ZβIodoenones and Related Reaction from Aryl Iodides and Internal Alkynes
290
RXN79 CrossCoupling of Organometallics with Terminal Alkynes and Iodotrimethysilane
292
RXN80 Preparation of αβUnsaturated Carbonyl Derivatives from Enol Silanes
294
RXN81 13Butadien2ylaminocyclization of Allenyl Tosylcarbamates
296
RXN82 Addition of Pronucleophiles on Aldehydes
298
RXN83 Allylation of Pronucleophiles with Allylstannanes
301
RXN84 Crosscoupling Carbonylation of Aryl Iodides with FiveMembered Cyclic Olefins
303
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About the author (1997)

Jean-Luc Malleron received his graduate degree from the school of chemistry at Montpellier and then went on to obtain his Ph.D. at the Université Paris Sud. Malleron has been Senior Research Fellow in medicinal chemistry at Rhône-Poulec Rorer Company since 1981.