Table Of ContentHandbook of Reagents
for Organic Synthesis
Catalyst Components for
Coupling Reactions
OTHER TITLES IN THIS COLLECTION
Fluorine-Containing Reagents
Edited by Leo A. Paquette
ISBN 978 0 470 02177 4
Reagents for Direct Functionalization for C–H Bonds
Edited by Philip L. Fuchs
ISBN 0 470 01022 3
Reagents for Glycoside, Nucleotide, and Peptide Synthesis
Edited by David Crich
ISBN 0 470 02304 X
Reagents for High-Throughput Solid-Phase and Solution-Phase
Organic Synthesis
Edited by Peter Wipf
ISBN 0 470 86298 X
Chiral Reagents for Asymmetric Synthesis
Edited by Leo A. Paquette
ISBN 0 470 85625 4
Activating Agents and Protecting Groups
Edited by Anthony J. Pearson and William R. Roush
ISBN 0 471 97927 9
Acidic and Basic Reagents
Edited by Hans J. Reich and James H. Rigby
ISBN 0 471 97925 2
Oxidizing and Reducing Agents
Edited by Steven D. Burke and Rick L. Danheiser
ISBN 0 471 97926 0
Reagents, Auxiliaries and Catalysts for C–C Bond Formation
Edited by Robert M. Coates and Scott E. Denmark
ISBN 0 471 97924 4
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Handbook of Reagents
for Organic Synthesis
Catalyst Components for
Coupling Reactions
Edited by
Gary A. Molander
University of Pennsylvania, Philadelphia, PA, USA
Copyright # 2008 John Wiley & Sons Ltd,
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e-EROS Editorial Board
Editor-in-Chief
Leo A. Paquette
The Ohio State University, Columbus, OH, USA
Executive Editors
David Crich
Wayne State University, Detroit, MI, USA
Philip L. Fuchs
Purdue University, West Lafayette, IN, USA
Gary Molander
University of Pennsylvania, Philadelphia, PA, USA
Contents
Preface ix 1-Butyl-3-methylimidazolium Hexafluorophosphate
([Bmim]PF6) 182
Introduction xi (R,S)-CAMPHOS 189
Carbonyl(chloro)bis(triphenylphosphine)rhodium(I) 190
Recent Review Articles and Monographs 1 Chloro(1,5-cyclooctadiene)rhodium(I) Dimer 199
1-Adamantyl-di-tert-butylphosphine 5 Chlorotris(triphenylphosphine)rhodium(I) 206
Benzylchlorobis(triphenylphosphine)palladium(II) 7 Cobalt(II) Chloride 218
[1,10-Biphenyl]-2-yldicyclohexylphosphine 8 Copper 222
Bis(acetonitrile)[(1,2,5,6-)-1,5-cyclooctadiene]- Copper(II) Acetate 226
rhodium(1þ),tetrafluoroborate(1-) 12 Copper(II) Acetylacetonate 232
Bis(acetonitrile)dichloropalladium(II) 15 Copper(I) Bromide 235
Bis(allyl)di--chlorodipalladium 31 Copper Bronze 242
(R,R)-1,2-Bis(aminocarbonylphenyl-20- Copper(II) Chloride 243
diphenylphosphino)cyclohexane 54 Copper(I) Chloride-Oxygen 250
Bis(benzonitrile)dibromopalladium(II) 59 Copper(II) Hydroxide 264
Bis(benzonitrile)dichloropalladium(II) 60 Copper(I) Iodide 264
Bis(bicyclo[2.2.1]hepta-2,5-diene)dichlorodirhodium 84 Copper(I) Iodide–Potassium Naphthalenide 275
Bis[(1R)-[1,10-binaphthalene]-2,20-diylbis[diphenyl- Copper(I) Iodide–Triethyl Phosphite 275
phosphine-P]]di--hydroxydirhodium 88 Copper(I) Oxide 276
Bis[1,2-bis(diphenylphosphino)ethane]palladium(0) 90 Copper(I) Trifluoromethanesulfonate 281
[[2,6-Bis[[(bis(1-methylethyl)phosphino-P]methyl]-3,5 [(1R,2R,3S,4S)-1,2,3,4-Cyclopentanetetrakis(methylene)]-
dimethylphenyl]methyl-C]trifluoroacetato-O)palladium 91 tetrakis[diphenyl]phosphine 303
Bis[(1,2,5,6-)-1,5-cyclooctadiene]di--hydroxydirhodium 92 Diacetatobis(tri-o-tolylphosphine)palladium(II) 307
Bis[(1,2,5,6-)-1,5-cyclooctadiene]di--methoxydirhodium 94 Dibromobis(triphenylphosphine)nickel(II) 307
Bis(1,5-cyclooctadiene)nickel(0) 95 Dibromobis(triphenylphosphine)palladium(II) 309
Bis[(1,2,5,6-)-1,5-cyclooctadiene] rhodium(1þ), 2-(Di-tert-butylphosphino)biphenyl 310
Hexafluoroantimonate(1 ) 114 Dicarbonyl(acetylacetonato) rhodium(I) 314
Bis(dibenzylideneacetone)palladium(0) 118 Dichloro[1,4-bis(diphenylphosphino)butane]nickel(II) 316
1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol- Dichloro[1,4-bis(diphenylphosphino)butane]palladium(II) 318
2-ylidene 124 Dichloro[1,2-bis(diphenylphosphino)ethane]palladium(II) 320
1,3-Bis(2,6-diisopropylphenyl)-imidazol-2-ylidene 126 Dichloro[1,10-bis(diphenylphosphino)ferrocene]-
Bis(1,1-dimethylethyl)[20,40,60-tris(1-methylethyl)[1,10- palladium(II) 321
biphenyl]-2-yl]phosphine and Dicyclohexyl[20,40,60-tris Dichlorobis(tricyclohexylphosphine)palladium 322
(1-methylethyl)[1,10-biphenyl]-2-yl]phosphine 127 Dichlorobis(triphenylphosphine)nickel(II) 326
(R)- & (S)-2,20-Bis(diphenylphosphino)-1,10-binaphthyl 130 Dichlorobis(triphenylphosphine)palladium(II) 332
1,4-Bis(diphenylphosphino)butane 141 Dichlorobis(tri-o-tolylphosphine)palladium(II) 343
(2R,3R)-2,3-Bis(diphenylphosphino)butane 142 Dichloro[2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis-
1,2-Bis(diphenylphosphino)ethane 144 (diphenylphosphino)butane]palladium(II) 345
1,10-Bis(diphenylphosphino)ferrocene 146 Dicyclohexyl(20,60-dimethoxy[1,10-biphenyl]-2-yl)-
Bis[2-(diphenylphosphino)phenyl]ether (DPE-phos) 155 phosphine (S-Phos) 346
1,3-Bis(diphenylphosphino)propane 161 2-Dicyclohexylphosphino-20-(N,N-dimethylamino)-
Bis(2-ethene)(2,4-pentanedionato-O,O0) rhodium 163 biphenyl 348
Bis(triphenylphosphine)[1,2-bis(diphenylphosphino)- (R)-1-[(1R)-1-(Dicyclohexylphosphino)ethyl]-2-
ethane]palladium(0) 165 (diphenylphosphino)-ferrocene, (2S)-1-[(1R)-1-
Bis(triphenylphosphine)nickel(0) 167 (Dicyclohexylphosphino)ethyl]-2-(diphenylphosphino)-
Bis(triphenylphosphine)palladium(II) acetate 168 ferrocene, (Josiphos) 353
Bis[tri(o-tolyl)phosphine]palladium 173 2-(20-Dicyclohexylphosphinophenyl)-2-methyl-
Bromo(o-tolyl)bis(triethylphosphine)nickel(II) 182 1,3-dioxolane 364
viii CONTENTS
1-(4,5-Dihydro-4-phenyl-2-oxazolyl)-2-(diphenyl- Palladium–Graphite 502
phosphino) ferrocene 365 Palladium Nanoparticles 503
(1,3-Diisopropylimidazol-2-ylidene)(3-chloropyridyl) Palladium(II) Trifluoroacetate 515
0
palladium(II) chloride (PEPPSI) 367 1,2,3,4,5-Pentaphenyl-1 -(di-tert-butylphosphino)
Dilithium Tetrachlorocuprate(II) 370 ferrocene (Q-Phos) 516
Dilithium Tetrachloropalladate(II) 375 Potassium Tetrachloropalladate(II) 519
0
(R)-N-[2-(N,N-Dimethylamino)ethyl]-N-methyl-1-[(S)-1 , Proazaphosphatranes 523
2-bis(diphenylphosphino)ferrocenyl]ethylamine 377 Silver(I) Oxide 527
(R)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]- Tetrakis(acetonitrile)copper(I) Perchlorate 533
ethylamine 380 Tetrakis(acetonitrile)copper(I) Tetrafluoroborate 537
(4S)-4-(1,1-Dimethylethyl)-2-1-[(11bS)dinaphtho- Tetrakis(acetonitrile)palladium Tetrafluoroborate 542
0 0
[2,1-d:1 ,2 f][1,3,2]-dioxaphosphepin-4-yloxy]-1- Tetrakis(triisopropyl phosphite)palladium(0) 547
methylethyl-4,5-dihydrooxazole 381 Tetrakis(triphenylphosphine)nickel(0) 548
(1R,2S,4R,5S)-2,5-Dimethyl-7-phenyl-7-phosphabi- Tetrakis(triphenylphosphine)palladium(0) 550
cyclo[2.2.1]heptane 384 Tri-tert-butylphosphine 559
(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[diphenyl- Tri-tert-butylphosphine Tetrafluoroborate 562
phosphine (Xantphos) 385 Tricyclohexylphosphine 566
0 0
2 -(Diphenylphosphino)-N,N-dimethyl[1,1 -binaphthalen]- Tri-2-furylphosphine (TFP) 569
2-amine 387 Trimethyl Phosphite 576
(S)-2-[2-(Diphenylphosphino)phenyl]-4-phenyloxazoline 391 Triphenylarsine 582
Encapsulated Palladium Catalysts 403 Triphenyl Phosphite 587
Hydrotetrakis(triphenylphosphine)rhodium 409 Tris(acetoacetonyl)cobalt 593
Iodo(phenyl)bis(triphenylphosphine)palladium(II) 413 Tris(acetonitrile)tricarbonyltungsten 595
Iron(III) Chloride 414 Tris(acetylacetonato)iron(III) 596
Lithium Trichloropalladate 423 Tris(dibenzoylmethide)iron(III) 600
(Maleic anhydride)bis(triphenylphosphine)palladium 425 Tris(dibenzylideneacetone)dipalladium–Chloroform 602
Merrifield-diphenylphosphine Palladium Complexes 430 Tris(triphenylphosphine)nickel(0) 607
Nickel 435 m-Trisulfonated Triphenylphosphine 609
Nickel(II) Acetylacetonate 436 Tri-o-Tolylphosphine 620
Nickel(II) Bromide 442 Zinc/Nickel Couple 625
II
Nickel-in-Charcoal (Ni /C) 444
Nickel(II) Chloride 447
(R,R)-( )-NORPHOS, (S,S)-(þ)-NORPHOS 451 List of Contributors 627
Palladium(II) Acetate 459
Palladium(II) Acetylacetonate 483 Reagent Formula Index 639
Palladium(II) Chloride 484
Palladium(II) Chloride–Silver(I) Acetate 502 Subject Index 643
General Abbreviations
