The Chemistry of Organozinc Compounds, 2 Part Set R-Zn

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The Patai Series publishes comprehensive reviews on all aspects of specific functional groups. Each volume contains outstanding surveys on theoretical and computational aspects, NMR, MS, other spectroscopic methods and analytical chemistry, structural aspects, thermochemistry, photochemistry, synthetic approaches and strategies, synthetic uses and applications in chemical and pharmaceutical industries, biological, biochemical and environmental aspects. To date, over 110 volumes have been published in the series. Recently Published Titles The chemistry of the Cyclopropyl Group (Volume 2) The chemistry of the Hydrazo, Azo and Azoxy Groups (Volume 2, 2 parts) The chemistry of Double-Bonded Functional Groups (Volume 3, 2 parts) The chemistry of Organophosphorus Compounds (Volume 4) The chemistry of Halides, Pseudo-Halides and Azides (Volume 2, 2 parts) The chemistry of the Amino, Nitro and Nitroso Groups (2 volumes, 2 parts) The chemistry of Dienes and Polyenes (2 volumes) The chemistry of Organic Derivatives of Gold and Silver The chemistry of Organic Silicon Compounds (2 volumes, 4 parts) The chemistry of Organic Germanium, Tin and Lead Compounds (Volume 2, 2 parts) The chemistry of Phenols (2 parts) The chemistry of Organolithium Compounds (2 volumes, 3 parts) The chemistry of Cyclobutanes (2 parts) The chemistry of Peroxides (Volume 2, 2 parts) The chemistry of Organozinc Compounds (2 parts) Forthcoming Titles The chemistry of Anilines The chemistry of Organomagnesium Compounds The Patai Series Online The Patai Series is available in electronic format on Wiley InterScience. All new titles will be published as online books and a growing list of older titles will be added every year. It is the ultimate goal that all titles published in the Patai Series will be available in electronic format. For more information see under Online Books on: www.interscience.wiley.com

The reaction mechanisms of zinc enzymes

(30)

Gudrun Schurer

Timothy Clark

Rudi van Eldik

Introduction

(1)

Structural Aspects

(5)

General Reaction Mechanisms

(1)

A Number of Enzymes

(15)

Class I: Oxidoreductases

(1)

Alcohol dehydrogenase

(1)

Superoxide dismutase

(1)

Class II: Transferases

(1)

Prenyl transferases

(2)

Class III: Hydrolases

(1)

Aminopeptidase

(2)

Carboxypeptidase

(2)

Thermolysin

(1)

β-Lactamase

(2)

Alkaline phosphatase

(1)

Phospholipase C

(1)

Class IV: Lyases

(1)

Carbonic anhydrase

(3)

Acknowledgment

(1)

References

(8)

Structural organozinc chemistry

(106)

Johann T. B. H. Jastrzebski

Jaap Boersma

Gerard van Koten

Introduction

(2)

Organozincates

(19)

Introduction

(1)

Tetraorganozincates [R4Zn]M2

(6)

Homoleptic Triorganozincates [R3Zn]M

(6)

Heteroleptic Triorganozincates [R2R',Zn]M

(6)

Dialkyl- and Diarylzinc Compounds

(29)

Donor-base-free, σ,σ-Bonded Homoleptic R2Zn and Heteroleptic RR'Zn Compounds

(7)

Diorganozinc Compounds Containing Multi-hapto Bonded Groups

(4)

Diorganozinc Compounds Containing Intramolecularly Coordinating Substituents

(6)

Donor -- Acceptor Complexes of Diorganozinc Compounds

(12)

Heteroleptic RZnY Compounds

(41)

Introduction

(1)

Monoorganozinc Cations

(2)

Monoorganozinc Compounds RZnY with Y = Halogen

(9)

Monoorganozinc Compounds RZnY with Y = OR

(13)

Monoorganozinc Compounds RZnY with Y = NR2

107

(11)

Monoorganozinc Compounds RZnY with Y = Other Heteroatom Bonded Group

118

(5)

Organozinc Compounds Containing a Zinc-Transition Metal Bond

123

(3)

Conclusions

126

(1)

References

127

(10)

Thermochemistry of organozinc compounds

137

(10)

Joel F. Liebman

Suzanne W. Slayden

Introduction: Scope and Definitions

137

(1)

Dialkylzinc Compounds

138

(5)

Enthalpies of Vaporization

138

(2)

Enthalpies of Formation

140

(2)

Bond Energies

142

(1)

Monoalkylzinc Species

143

(1)

Dimethylzinc Radical Cation and Methylzinc Cation

144

(1)

Zinc-Cyanide Complexes

144

(1)

References and Notes

144

(3)

67Zn NMR, a tool for coordination chemistry problems

147

(16)

Athanassios G. Coutsolelos

Georgios A. Spyroulias

Introduction

147

(1)

1H and 13C NMR Spectroscopy of Organometallic Compounds

148

(2)

67Zn NMR Spectroscopy of Organometallic Compounds and Biomacromolecules

150

(1)

Theoretical Introduction and Technical Difficulties

151

(1)

Solid-State NMR

152

(1)

Interest for Bioinorganic Chemistry

153

(2)

Interest for Material--Solid-State Chemistry

155

(1)

Applications

156

(2)

References

158

(5)

Mass spectrometry of organozinc compounds

163

(30)

Sergiu P. Palii

Dmitri V. Zagorevskii

Abbreviations

164

(1)

Introduction

164

(2)

Mass Spectrometry of Organozinc Compounds

166

(13)

Dialkylzinc and Dihaloalkylzinc Compounds

166

(5)

Other Organozinc Compounds with the General Formula ZnR2

171

(1)

Miscellaneous Complexes Containing a Zn--C Bond

172

(1)

Cubane-like zinc-containing clusters

172

(2)

Binuclear and dimeric zinc complexes

174

(2)

Monomeric RZnL complexes (L = polydentate ligand)

176

(1)

Other species containing organozinc fragments

177

(2)

Organozinc Ion Structure and Energetics

179

(6)

Energetics and Photodissociation Studies

179

(2)

Gas Phase Ion/Molecule Reactions

181

(3)

In silico Studies of Organozinc Ion Structures

184

(1)

Other Studies Involving Mass Spectrometry

185

(2)

Mass Spectrometric Investigation of Pyrolysis of Zinc-containing Species

185

(2)

Monitoring of Organometallic Vapor Phase Epitaxy by Mass Spectrometry

187

(1)

Conclusions

187

(1)

References

187

(6)

Dynamic behavior of organozinc compounds

193

(44)

Albert Guijarro

Introduction

194

(1)

Dynamics of Carbon--Zinc Bond Exchange: C--Zn Exchange

195

(22)

Intermolecular C--Zn Exchange

195

(1)

Alkyl--Zn exchange in dialkylzinc compounds

195

(1)

Alkyl--Zn exchange in dimethylzinc and related compounds

195

(4)

Alkyl--Zn exchange in primary, secondary and other dialkylzinc compounds

199

(1)

Exchange with aryl, alkenyl and alkynylzinc compounds

200

(2)

Alkyl--Zn exchange in organozinc salts

202

(1)

Alkyl--Zn exchange in organozinc salts--diorganozinc compounds

202

(1)

The Schlenk equilibrium

203

(1)

Alkyl exchange in zincates

204

(1)

Metallotropic Exchange in Organozinc Reagents

205

(1)

Allylzinc reagent dynamics

205

(3)

2,4-Dienylzinc reagent dynamics

208

(2)

Zincocene dynamics

210

(1)

Alkyl-Zn Exchange with Other Organometallic Compounds

211

(1)

Methyl--Zn exchange between Me2Zn and MenM, M = Zn, Cd, Hg, Mg, In

211

(3)

Influence of the alkyl group on the exchange rate

214

(1)

Alkyl--Zn exchange with organoboranes

215

(2)

Dynamics of Inversion at Carbon Bonded to Zinc: C--Zn Inversion

217

(13)

Inversion at a Primary Alkyl Carbon Bonded to Zinc

217

(5)

Inversion at a Secondary Alkyl Carbon Bonded to Zinc

222

(5)

Vinylic Carbon Bonded to Zinc

227

(1)

Inversion at Benzylic Carbon Bonded to Zinc

227

(2)

Inversion at Allylic and Propargylic Carbon Bonded to Zinc

229

(1)

Appendix

230

(3)

Obtention of the Different Activation Parameters by NMR

230

(2)

Relationships between Activation Parameters

232

(1)

The Arrhenius and Eyring equations

232

(1)

References

233

(4)

Cyclopropanation mediated by zinc organometallics

237

(50)

Andre B. Charette

Introduction

237

(1)

Preparation and Structure of Zinc Carbenoids

238

(7)

Unsubstituted Halomethylzinc Carbenoids

238

(2)

α-Substituted Halomethylzinc Carbenoids

240

(2)

Solid and Solution Structures of Halomethylzinc Reagents

242

(3)

Mechanism of the Cyclopropanation of Alkenes Using Zinc Carbenoids

245

(1)

Synthetic Scope of the Cyclopropanation Using Zinc Carbenoids

246

(35)

Nature of the Reaction Solvent, Additives and Reaction Temperature

246

(1)

Achiral Alkenes

247

(9)

Stereoselective Cyclopropanation of Chiral Alkenes

256

(1)

Stereoselective cyclopropanation of cyclic alkenes

257

(4)

Stereoselective cyclopropanation of acyclic alkenes

261

(5)

Stereoselective Cyclopropanation of Alkenes using Chiral Auxiliaries

266

(7)

Stereoselective Cyclopropanation of Alkenes using Stoichiometric Chiral Reagents

273

(6)

Stereoselective Cyclopropanation of Alkenes using Chiral Catalysts

279

(2)

Conclusion

281

(2)

References

283

(4)

Functionalized organozinc compounds

287

(108)

Paul Knochel

Helena Leuser

Liu-Zhu Gong

Sylvie Perrone

Florian F. Kneisel

Introduction

288

(1)

Methods of Preparation of Polyfunctional Organozinc Reagents

288

(34)

Classification

288

(1)

Preparation of Polyfunctional Organozinc Halides

289

(1)

Preparation by the oxidative addition to zinc metal

289

(7)

Preparation of organozinc halides using transmetalation reactions

296

(12)

Preparation of Diorganozincs

308

(1)

Preparation via an I/Zn exchange

308

(3)

The boron--zinc exchange

311

(5)

Hydrozincation of alkenes

316

(1)

Diverse Methods of Preparation of Allylic Zinc Reagents

317

(2)

Preparation of Lithium Triorganozincates

319

(3)

Reactions of Organozinc Reagents

322

(57)

Uncatalyzed Reactions

323

(10)

Copper(I) Catalyzed Reactions

333

(1)

Substitution reactions

334

(12)

Acylation reactions

346

(3)

Addition reactions

349

(3)

Michael additions

352

(9)

Palladium and Nickel Catalyzed Reactions

361

(9)

Reactions Catalyzed by Titanium and Zirconium(IV) Complexes

370

(8)

Reactions of Zinc Organometallics Catalyzed by Cobalt, Iron or Manganese Complexes

378

(1)

Conclusion

379

(1)

References and Notes

379

(16)

Photochemical transformations involving zinc porphyrins and phthalocyanines

395

(26)

Mathias O. Senge

Natalia N. Sergeeva

Abbreviations

396

(1)

Introduction

396

(1)

Basic Photochemistry of Porphyrins

397

(1)

General Concepts and Theoretical Background

397

(1)

Stability and Degradation

398

(1)

Donor--Acceptor Compounds for Pet

398

(8)

Electron Transfer Studies

398

(1)

Current Trends

399

(1)

Electron transfer compounds with novel acceptor groups

399

(3)

Light-harvesting complexes

402

(1)

Reaction center models

402

(1)

Current synthetic concepts

402

(3)

Materials and formulations

405

(1)

Applied Photochemistry

406

(6)

Use as Pigments

406

(1)

Photonics

407

(1)

Photosensitization Reactions

407

(1)

General principle

407

(1)

Photovoltaic applications

407

(2)

Medicinal use in photodynamic therapy

409

(2)

Chemical uses

411

(1)

Other Applications

412

(1)

Acknowledgment

412

(1)

References

412

(9)

Synthesis and reactions of allenylzinc reagents

421

(36)

James A. Marshall

Zincation of Propargylic Bromides

421

(1)

Mechanistic Studies

422

(3)

Regiochemistry of Additions to Aldehydes and Ketones

425

(1)

Stereochemistry of Additions

425

(2)

Transition State Calculations

427

(1)

Reagent Regioselectivity

428

(2)

Iodoallene-Derived Reagents

430

(2)

Configurational Stability

432

(1)

Allenyl Alkylzinc Reagents

432

(3)

Coupling of Allenylzinc Bromide Reagents with Aryl and Vinyl Halides

435

(1)

Palladiozincation of Propargylic Mesylates

435

(3)

Double Diastereoselection

438

(4)

Applications to Natural Product Synthesis

442

(4)

Additions to Imines and Aldehydes

446

(2)

Kinetic Resolution of Chiral Allenylzinc Reagents

448

(1)

Amine-Substituted Allenylzinc Reagents

449

(2)

Additions to Sulfoximines

451

(1)

Additions of Chloroallenylzinc Reagents to Aldehydes and Imines

451

(3)

References

454

(3)

Palladium- or nickel-catalyzed cross-coupling reactions with organozincs and related organometals

457

(98)

El-ichi Negishi

Qian Hu

Zhihong Huang

Guangwei Wang

Ning Yin

Introduction

459

(8)

Overview of the Pd- or Ni-Catalyzed Cross-Coupling of Organozincs

467

(16)

Countercations (M)

467

(1)

Transmetallation

468

(1)

Oxidative zincation

469

(1)

Zn--halogen exchange

470

(1)

Zn--hydrogen exchange

470

(1)

Hydrozincation

470

(1)

Carbozincation

471

(2)

Other methods of preparation of organozincs

473

(1)

Leaving Groups (X)

473

(2)

Pd or Ni Catalysts and Ligands (L)

475

(1)

Triphenylphosphine as an inexpensive and widely applicable prototypical phosphine

475

(1)

Sterically and electronically modified monodentate triarylphosphines, such as tris(2-furyl)phosphine and tris(o-tolyl)phosphine

476

(1)

Bidentate bis(α,ω-diphenylphosphino)alkanes, bis(1,1'-diphenylphosphino)ferrocene (dppf), bis(o,o'-diphenylphosphino)phenyl ether (DPEphos) and related chelating phosphines

476

(1)

Bulky trialkyl- and dialkylarylphosphines

477

(1)

Non-phosphine ligands

477

(3)

Binary ligand combinations

480

(1)

Cocatalysts or Additives

481

(1)

Solvents

481

(2)

Recent Advances in the Pd- or Ni-Catalyzed Cross-Coupling with Organometals Containing Zn, Mg, Al and Zr

483

(61)

Aryl--Aryl, Aryl--Alkenyl and Alkenyl--Aryl Coupling Reactions

483

(1)

Aryl-aryl coupling

483

(1)

Heterosubstituted arylzincs

484

(2)

Aryl chlorides

486

(1)

Asymmetric synthesis of biaryls

487

(1)

Aryl-alkenyl and alkenyl-aryl coupling

487

(5)

Alkenyl--Alkenyl Coupling

492

(1)

Overview

492

(1)

Recent advances

492

(8)

Pd-catalyzed Alkynylation

500

(1)

General discussion

500

(1)

Comparison of various protocols for Pd-catalyzed alkynylation

500

(1)

Availability of two complementary protocols

500

(1)

Direct synthesis of terminal alkynes by the use of ethynylmetals

501

(1)

Pd-catalyzed alkynylation with alkynes containing electron-withdrawing substituents

501

(1)

Use of alkenyl electrophiles that are prone to side reactions

501

(1)

Use of sterically hindered, relatively unreactive organic electrophiles

501

(1)

Current scope of protocol II involving the use of preformed alkynylmetals

501

(2)

Current scope of Pd-catalyzed alkynylation with alkynylzincs with respect to electrophilic coupling partners

503

(1)

Alkynyl--alkynyl coupling

504

(1)

Allyl, benzyl, propargyl and allenyl electrophiles

504

(1)

Alkynyl--acyl coupling

505

(1)

Recent advances in the Pd-catalyzed alkynylation

506

(1)

Pd-catalyzed alkynyl--alkenyl coupling with 1,1-dihalo-1-alkenes

507

(1)

Pd-catalyzed alkynyl--alkenyl coupling with 1,2-dihaloethylenes

507

(5)

Pd-catalyzed α-alkynylation of α-haloenones and related electrophiles

512

(4)

Synthesis of natural products via Pd-catalyzed alkynylation with alkynylmetals containing Zn or Mg

516

(1)

Pd- or Ni-catalyzed Allylation, Benzylation and Propargylation (Allenylation)

516

(1)

Overview

516

(2)

Allyl electrophiles

518

(1)

Benzyl electrophiles

519

(1)

Propargyl and allenyl electrophiles

519

(1)

Allylzincs and related allylmetals

519

(1)

Benzylzincs

519

(1)

Propargylzincs or allenylzincs

520

(1)

Recent advances

520

(1)

Pd-catalyzed alkynyl--allyl and alkynyl--benzyl coupling reactions

520

(1)

Pd-catalyzed propargyl (or allenyl)--aryl and propargyl (or allenyl)-allyl coupling reactions

521

(2)

Synthesis of natural products

523

(1)

Heterocycles

523

(1)

Pd- or Ni-catalyzed Alkylation

524

(1)

General discussion

524

(1)

Discovery and early development of the Pd-catalyzed alkylation

525

(1)

Pd- or Ni-catalyzed alkylation with alkyl electrophiles

526

(1)

Recent advances in the Pd- or Ni-catalyzed alkylation with alkylmetals

526

(1)

Metal countercations, leaving groups and catalysts

526

(2)

Synthesis of natural products via Pd- or Ni-catalyzed alkylation with alkylmetals containing Zn or Mg

528

(1)

Pd- or Ni-catalyzed alkylation with alkyl halides and related electrophiles

528

(14)

Acylation and Other Carbon--Carbon Bond Forming Reactions Catalyzed by Pd or Ni

542

(1)

Pd- or Ni-catalyzed acylation of organozincs

542

(2)

Pd- or Ni-catalyzed cyanation

544

(1)

Acknowledgment

544

(1)

References

545

(10)

Enantioselective addition of organozinc compounds

555

(40)

Kenso Soai

Tsuneomi Kawasaki

Itaru Sato

Introduction

556

(1)

The Mechanism of Catalysis for Diorganozinc Addition to Carbonyl Compounds

556

(4)

Enantioselective Addition of Dialkylzincs to Aldehydes using Lewis Base Catalysts

557

(2)

Enantioselective Addition of Dialkylzincs using Lewis Acid Catalysts

559

(1)

Enantioselective Addition of Organozincs to Carbonyl Compounds

560

(9)

Asymmetric Addition of Dialkylzincs and Functionalized Diorganozincs

560

(1)

Enantioselective Addition of Diorganozincs to Ketones

561

(2)

Enantioselective Alkenylation of Aldehydes and Ketones

563

(2)

Enantioselective Addition of Alkynylzincs to Aldehydes and Ketones

565

(1)

Asymmetric Aryl Transfer Reaction to Carbonyl Compounds

566

(2)

Enantioselective Conjugate Addition of Dialkylzincs to Enones

568

(1)

Enantioselective Addition of Diorganozincs to Imine Derivatives

569

(4)

Asymmetric Amplification

573

(3)

Asymmetric Autocatalysis in the Asymmetric Addition of Dialkylzincs to Aldehydes

576

(8)

Asymmetric Autocatalysis with High Enantioselectivity

576

(2)

Asymmetric Autocatalysis with Amplification of Chirality

578

(2)

Asymmetric Autocatalysis using Chiral Initiators

580

(1)

Asymmetric Autocatalysis using Circularly Polarized Light as a Sole Chiral Factor

581

(2)

Stochastic Production of S- and R-Enantiomers without Adding a Chiral Source by Asymmetric Autocatalysis: Spontaneous Absolute Asymmetric Synthesis

583

(1)

Conclusion

584

(2)

Acknowledgment

586

(1)

References

586

(9)

Rearrangements of organozinc compounds

595

(46)

Varinder K. Aggarwal

Knut Sommer

1,2-Metallate Rearrangements

596

(18)

Introduction

596

(1)

Reactions of 1,1-Dihalo Compounds with Triorganozincates

596

(1)

1,1-Dihaloalkenes

597

(1)

1,1-Dihalocyclopropanes

598

(2)

1,1-Dihaloalkanes

600

(2)

1,2-Migrations with Loss of a Leaving Group Attached to a Remote Carbon

602

(1)

Propargylic and homopropargylic substrates

602

(2)

Benzylic substrates

604

(1)

Methylene Homologations

605

(1)

Methylene homologations of organometallic reagents using organozincs

605

(1)

Methylene homologations in allene and olefin synthesis

606

(5)

Asymmetric reactions of homologated organozincs with aldehydes and imines

611

(3)

Reactions Involving 1,1-Dimetallic Species

614

(1)

Other Types of Rearrangements

614

(22)

Allylmetallation of Alkenyl and Alkynyl Metals

614

(1)

Allylmetallation of alkenyl metals

614

(9)

Allylmetallation of alkynyl metals

623

(3)

Computational results on the reaction mechanism

626

(1)

The Reformatsky Reaction

627

(1)

Fritsch--Buttenberg--Wiechell Rearrangement

627

(2)

Zinca-Ene-Allene and Zinc-Enolate Cyclizations

629

(5)

The Rearrangement of 1-Trimethylsilyl-2-propenylzinc Reagents

634

(2)

Conclusions

636

(1)

References and Notes

636

(5)

1,1-Bismetallated species

641

(44)

Seijiro Matsubara

Introduction

641

(1)

Preparation of sp3-Geminated Organodizinc Reagents

642

(8)

By Dihalomethane and Zinc

643

(2)

By Dihaloalkane and Zinc

645

(1)

By Heteroatom-substituted Dihaloalkane and Zinc

646

(1)

Via Carbometallation

647

(3)

Reaction of sp3-Geminated Organodizinc Reagents

650

(27)

Methylenation

651

(6)

Alkylidenation

657

(2)

Synthesis of Alkenyl-silane, -germane and -borane

659

(1)

Sequential Reaction with Two Electrophiles

659

(8)

Diastereoselective Construction of Carbon Skeleton by the Gaudemar/Normant Coupling

667

(4)

Nucleophilic Cyclopropanation

671

(3)

Pinacolone Rearrangement with Unusual Diastereospecificity

674

(1)

1,1-Dimetal Species from Zincated Hydrazone and Alkenylmetal

675

(1)

gem-Dizincio Reagent Working as Carbenoid

676

(1)

Preparation and Reaction of sp2-Geminated Organodizinc Reagents

677

(3)

Conclusion

680

(1)

References

680

(5)

The chemistry of organozincate compounds

685

(28)

Toshiro Harada

Introduction

685

(1)

Preparation of Zincates

686

(4)

Preparation of Zincates by Ate-Complex Formation

686

(1)

Preparation of Mixed Zincates by Metalation

687

(1)

Preparation of Mixed Zincates by Halogen--Zinc Exchange Reaction

688

(2)

Reaction of Zincates

690

(19)

Carbonyl Addition and Ring Opening of Epoxides

690

(1)

Conjugate Addition to α,β-Unsaturated Compounds

690

(4)

1,2-Migration of Zincate Carbenoids

694

(5)

1,2-Migration of Alkynylzincates and Arylzincates

699

(7)

Generation of Benzynes

706

(1)

Cross-coupling Reaction

707

(2)

Concluding Remarks

709

(1)

References

709

(4)

Fluorinated organozinc reagents

713

(42)

Charles R. Davis

Donald J. Burton

Introduction

714

(1)

Fluoroalkenylzinc Reagents

714

(18)

Method (1): Capture of Vinyllithium Reagents at Low Temperatures

714

(4)

Method (2): In Situ Capture of Vinyllithium Reagents at Ambient Temperatures

718

(4)

Method (3): Insertion of Zn° into The Carbon--Halogen Bond

722

(3)

Stereospecific preparation of fluorinated styrenes

725

(2)

Preparation of 1,1,2-trifluoro-2-trimethylsilylethylene

727

(1)

Stereospecific preparation of fluorinated dienes

727

(2)

Allylation

729

(1)

Acylation

729

(1)

Preparation of functionalized CF3-containing compounds

730

(1)

Allene formation

730

(2)

Preparation of polymer precursor

732

(1)

Perfluoroaryl Zinc Reagents

732

(1)

Fluorinated Allyl and Propargylzinc Reagents

733

(3)

Perfluoroalkynylzinc Reagents

736

(2)

Perfluoroalkylzinc Reagents

738

(6)

Dialkoxyphosphinyldifluoromethylzinc Reagents

744

(3)

Carboalkoxydifluoromethylenezinc Reagents

747

(3)

References

750

(5)

Electrochemical generation and reaction of zinc reagents

755

(42)

Jacques Perichon

Corinne Gosmini

Olivier Buriez

Introduction

756

(2)

Electrochemical Generation of a Reactive Zinc for the Formation of Stable or Transient Organozinc Reagents and Their Reactivity

758

(11)

Electrochemical Formation of Reactive Zinc

758

(2)

Synthesis of Stable or Transient Organozinc Species and their Reactivity

760

(1)

From electrolytic zinc

760

(5)

From activation of massive zinc

765

(1)

Synthetic applications to the Blaise reaction

765

(1)

Reformatsky-type reactions

766

(1)

Allylation of carbonyl compounds

766

(2)

Synthesis of benzylic zinc species and their reactivity towards aldehydes

768

(1)

Conclusion

769

(1)

Electrochemical Preparation of Organozinc Reagents Using Nickel Or Cobalt Catalysis

769

(25)

Introduction

769

(2)

Electrochemical Preparation of Organozinc Compounds using Nickel as Catalyst

771

(1)

From aromatic halides

771

(1)

From bromothiophene

772

(1)

Mechanism of the electrochemical conversion of aryl halides to arylzinc compounds by nickel catalysis

773

(3)

Reactivity of electrochemically prepared arylzinc compounds via a nickel catalysis

776

(1)

Reaction with cyclohex-2-en-1-one

776

(1)

Reaction with allyl halides

776

(1)

With trifluoroacetic anhydrides

777

(1)

With aryl halides: synthesis of unsymmetrical biaryls

777

(2)

Polymerization of 3-methylthiophene

779

(1)

With 2-halogenopyridine

780

(1)

Electrochemical Preparation of Organozinc Compounds using Cobalt Halides as Catalysts

781

(1)

Electrochemical behavior of cobalt halides CoX2 (X = Br, Cl)

782

(1)

In a DMF--or a MeCN--pyridine (v/v = 9/1) mixture

782

(1)

In acetonitrile

783

(2)

Electrosynthesis of aryl- or heteroarylzinc compounds

785

(1)

In DMF/pyridine or CH3CN/pyridine as solvent

786

(3)

In pure acetonitrile

789

(1)

Reactivity of electrochemically prepared arylzinc compounds via a cobalt catalysis

790

(1)

Cross-coupling reaction with aryl halide

790

(1)

Synthesis of alternating π-conjugated copolymers

790

(1)

Synthesis of functionalized 4-phenylpyridines

791

(1)

Synthesis of aromatic ketones

791

(2)

Arylation of activated olefins

793

(1)

Conclusion

794

(1)

References

795

(2)

The chemistry of zinc enolates

797

(66)

Marco Lombardo

Claudio Trombini

General and Theoretical Aspects

797

(2)

The Reformatsky Reaction

799

(20)

Introduction

799

(2)

Activation Techniques for Zinc Metal

801

(1)

Chemical or physical activation of commercial zinc powders

801

(1)

Preparation of highly reactive forms of zinc metal

802

(1)

Electrochemical Reformatsky reaction promoted by sacrificial anodes

803

(2)

Alternative metals for the Reformatsky reaction

805

(3)

Recent Applications of the Reformatsky Reaction

808

(1)

Racemic reactions

808

(3)

Enantioselective reactions

811

(1)

Diastereoselective reactions

812

(7)

The Gilman--Speeter Reaction

819

(8)

Further Electrophiles for Reformatsky Reagents

827

(10)

Carboxylic Acid Derivatives

827

(2)

Electron-poor Carbon--Carbon Double Bonds

829

(4)

Phosphorus electrophiles

833

(1)

Transition metal-catalysed coupling reactions

833

(4)

Alternative Routes to Zinc Enolates

837

(11)

Lithiation/Transmetallation Protocols

837

(5)

Zinc Enolates from Diethylzinc as Metal Source

842

(6)

Zinc Dienolates

848

(6)

Conclusions

854

(1)

References

854

(9)

Carbozincation of alkenes and alkynes

863

(116)

Edwige Lorthiois

Christophe Meyer

Introduction

864

(1)

Reactivity of Alkyl and Aryl Organozinc Reagents

865

(25)

Uncatalyzed Intermolecular Carbozincations

865

(1)

Intermolecular additions to alkynes

865

(1)

Intermolecular additions to alkenes

866

(2)

Uncatalyzed Intramolecular Carbozincations

868

(1)

Intramolecular carbozincation of alkynes

868

(2)

Intramolecular carbozincation of alkenes

870

(6)

Transition Metal-catalyzed or promoted Carbozincations

876

(1)

Palladium- and nickel-catalyzed intramolecular carbozincations

876

(2)

Transition metal-catalyzed/promoted intermolecular carbozincations of alkynes

878

(1)

Zirconium-promoted carbozincations

878

(1)

Nickel-catalyzed carbozincations

879

(2)

Transition metal-catalyzed intermolecular carbozincations of alkenes

881

(1)

Iron-catalyzed carbozincations

881

(1)

Palladium-catalyzed carbozincations

882

(2)

Zirconium-catalyzed ethylzincation

884

(1)

Titanium-catalyzed carbozincation of enynes

884

(1)

Multi-component Reactions involving Organozinc Reagents

885

(5)

Carbozincation of a 1,3-Dipolar Intermediate

890

(1)

Reactivity of Allylic Organozinc Reagents

890

(55)

Intermolecular Allylzincation of Alkenes

891

(1)

Uncatalyzed reactions

891

(7)

Transition metal-catalyzed reactions

898

(1)

Intermolecular Allylzincation of Alkynes

898

(1)

Uncatalyzed reactions

898

(3)

Transition metal-promoted allylzincation of disubstituted alkynes

901

(1)

Intramolecular Zinc--Ene Reactions

901

(1)

Type I zinc-ene reactions

902

(3)

Type II zinc-ene reactions

905

(3)

Allylzincation of Alkenylmetals

908

(1)

Synthesis and reactivity of gem-diorganometallic species

908

(5)

Theoretical studies

913

(2)

Diastereoselective allylzincations of alkenylmetals

915

(1)

Mutual diastereoselection

915

(2)

Substrate-induced diastereoselection

917

(10)

Transformation of the sp3 dimetallated carbon into a stereocenter

927

(5)

Allylzincation of Allenylmetals

932

(4)

Allylzincation of Alkynylmetals

936

(1)

Reactivity of allylic organozinc reagents towards metallated alkynes

936

(4)

Functionalization of the alkenyl 1,1-diorganometallic reagents

940

(5)

Reactivity of Allenylzinc Reagents

945

(11)

Intermolecular Carbozincations of Alkynes and Alkenes

945

(1)

Addition to alkynylmetals

945

(2)

Addition to alkenylmetals

947

(1)

Intramolecular Carbozincations of Alkynes and Alkenes

948

(1)

Intramolecular carbozincations of alkynes

948

(2)

Intramolecular carbozincations of alkenes

950

(6)

Reactivity of Zinc Enolates and AZA-Enolates

956

(15)

Addition of Zinc Enolates to Alkynes

956

(3)

Addition of Zinc Enolates to Alkenes

959

(1)

Intramolecular reactions

959

(5)

Intermolecular additions of zinc enolates to alkenes

964

(7)

Conclusion

971

(1)

References

972

(7)

Author index

979

(74)

Subject index

1053

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The Chemistry of Organozinc Compounds, 2 Part Set R-Zn

Summary

Author Biography

Table of Contents

Supplemental Materials

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The Chemistry of Organozinc Compounds, 2 Part Set R-Zn

Summary

Author Biography

Table of Contents

Supplemental Materials

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