|
The reaction mechanisms of zinc enzymes |
|
|
1 | (30) |
|
|
|
|
|
|
|
|
|
2 | (1) |
|
|
|
2 | (5) |
|
General Reaction Mechanisms |
|
|
7 | (1) |
|
|
|
8 | (15) |
|
|
|
8 | (1) |
|
|
|
8 | (1) |
|
|
|
9 | (1) |
|
|
|
10 | (1) |
|
|
|
10 | (2) |
|
|
|
12 | (1) |
|
|
|
12 | (2) |
|
|
|
14 | (2) |
|
|
|
16 | (1) |
|
|
|
16 | (2) |
|
|
|
18 | (1) |
|
|
|
19 | (1) |
|
|
|
20 | (1) |
|
|
|
20 | (3) |
|
|
|
23 | (1) |
|
|
|
23 | (8) |
|
Structural organozinc chemistry |
|
|
31 | (106) |
|
Johann T. B. H. Jastrzebski |
|
|
|
|
|
|
|
|
32 | (2) |
|
|
|
34 | (19) |
|
|
|
34 | (1) |
|
Tetraorganozincates [R4Zn]M2 |
|
|
35 | (6) |
|
Homoleptic Triorganozincates [R3Zn]M |
|
|
41 | (6) |
|
Heteroleptic Triorganozincates [R2R',Zn]M |
|
|
47 | (6) |
|
Dialkyl- and Diarylzinc Compounds |
|
|
53 | (29) |
|
Donor-base-free, σ,σ-Bonded Homoleptic R2Zn and Heteroleptic RR'Zn Compounds |
|
|
53 | (7) |
|
Diorganozinc Compounds Containing Multi-hapto Bonded Groups |
|
|
60 | (4) |
|
Diorganozinc Compounds Containing Intramolecularly Coordinating Substituents |
|
|
64 | (6) |
|
Donor -- Acceptor Complexes of Diorganozinc Compounds |
|
|
70 | (12) |
|
Heteroleptic RZnY Compounds |
|
|
82 | (41) |
|
|
|
82 | (1) |
|
|
|
83 | (2) |
|
Monoorganozinc Compounds RZnY with Y = Halogen |
|
|
85 | (9) |
|
Monoorganozinc Compounds RZnY with Y = OR |
|
|
94 | (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) |
|
|
|
126 | (1) |
|
|
|
127 | (10) |
|
Thermochemistry of organozinc compounds |
|
|
137 | (10) |
|
|
|
|
|
Introduction: Scope and Definitions |
|
|
137 | (1) |
|
|
|
138 | (5) |
|
Enthalpies of Vaporization |
|
|
138 | (2) |
|
|
|
140 | (2) |
|
|
|
142 | (1) |
|
|
|
143 | (1) |
|
Dimethylzinc Radical Cation and Methylzinc Cation |
|
|
144 | (1) |
|
|
|
144 | (1) |
|
|
|
144 | (3) |
|
67Zn NMR, a tool for coordination chemistry problems |
|
|
147 | (16) |
|
Athanassios G. Coutsolelos |
|
|
|
|
|
|
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) |
|
|
|
152 | (1) |
|
Interest for Bioinorganic Chemistry |
|
|
153 | (2) |
|
Interest for Material--Solid-State Chemistry |
|
|
155 | (1) |
|
|
|
156 | (2) |
|
|
|
158 | (5) |
|
Mass spectrometry of organozinc compounds |
|
|
163 | (30) |
|
|
|
|
|
|
|
164 | (1) |
|
|
|
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) |
|
|
|
187 | (1) |
|
|
|
187 | (6) |
|
Dynamic behavior of organozinc compounds |
|
|
193 | (44) |
|
|
|
|
|
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) |
|
|
|
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) |
|
|
|
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) |
|
|
|
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) |
|
|
|
233 | (4) |
|
Cyclopropanation mediated by zinc organometallics |
|
|
237 | (50) |
|
|
|
|
|
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) |
|
|
|
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) |
|
|
|
281 | (2) |
|
|
|
283 | (4) |
|
Functionalized organozinc compounds |
|
|
287 | (108) |
|
|
|
|
|
|
|
|
|
|
|
|
|
288 | (1) |
|
Methods of Preparation of Polyfunctional Organozinc Reagents |
|
|
288 | (34) |
|
|
|
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) |
|
|
|
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) |
|
|
|
323 | (10) |
|
Copper(I) Catalyzed Reactions |
|
|
333 | (1) |
|
|
|
334 | (12) |
|
|
|
346 | (3) |
|
|
|
349 | (3) |
|
|
|
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) |
|
|
|
379 | (1) |
|
|
|
379 | (16) |
|
Photochemical transformations involving zinc porphyrins and phthalocyanines |
|
|
395 | (26) |
|
|
|
|
|
|
|
396 | (1) |
|
|
|
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) |
|
|
|
399 | (1) |
|
Electron transfer compounds with novel acceptor groups |
|
|
399 | (3) |
|
Light-harvesting complexes |
|
|
402 | (1) |
|
|
|
402 | (1) |
|
Current synthetic concepts |
|
|
402 | (3) |
|
Materials and formulations |
|
|
405 | (1) |
|
|
|
406 | (6) |
|
|
|
406 | (1) |
|
|
|
407 | (1) |
|
Photosensitization Reactions |
|
|
407 | (1) |
|
|
|
407 | (1) |
|
Photovoltaic applications |
|
|
407 | (2) |
|
Medicinal use in photodynamic therapy |
|
|
409 | (2) |
|
|
|
411 | (1) |
|
|
|
412 | (1) |
|
|
|
412 | (1) |
|
|
|
412 | (9) |
|
Synthesis and reactions of allenylzinc reagents |
|
|
421 | (36) |
|
|
|
Zincation of Propargylic Bromides |
|
|
421 | (1) |
|
|
|
422 | (3) |
|
Regiochemistry of Additions to Aldehydes and Ketones |
|
|
425 | (1) |
|
Stereochemistry of Additions |
|
|
425 | (2) |
|
Transition State Calculations |
|
|
427 | (1) |
|
|
|
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) |
|
|
|
454 | (3) |
|
Palladium- or nickel-catalyzed cross-coupling reactions with organozincs and related organometals |
|
|
457 | (98) |
|
|
|
|
|
|
|
|
|
|
|
|
|
459 | (8) |
|
Overview of the Pd- or Ni-Catalyzed Cross-Coupling of Organozincs |
|
|
467 | (16) |
|
|
|
467 | (1) |
|
|
|
468 | (1) |
|
|
|
469 | (1) |
|
|
|
470 | (1) |
|
|
|
470 | (1) |
|
|
|
470 | (1) |
|
|
|
471 | (2) |
|
Other methods of preparation of organozincs |
|
|
473 | (1) |
|
|
|
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) |
|
|
|
477 | (3) |
|
Binary ligand combinations |
|
|
480 | (1) |
|
|
|
481 | (1) |
|
|
|
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) |
|
|
|
483 | (1) |
|
Heterosubstituted arylzincs |
|
|
484 | (2) |
|
|
|
486 | (1) |
|
Asymmetric synthesis of biaryls |
|
|
487 | (1) |
|
Aryl-alkenyl and alkenyl-aryl coupling |
|
|
487 | (5) |
|
Alkenyl--Alkenyl Coupling |
|
|
492 | (1) |
|
|
|
492 | (1) |
|
|
|
492 | (8) |
|
Pd-catalyzed Alkynylation |
|
|
500 | (1) |
|
|
|
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) |
|
|
|
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) |
|
|
|
516 | (2) |
|
|
|
518 | (1) |
|
|
|
519 | (1) |
|
Propargyl and allenyl electrophiles |
|
|
519 | (1) |
|
Allylzincs and related allylmetals |
|
|
519 | (1) |
|
|
|
519 | (1) |
|
Propargylzincs or allenylzincs |
|
|
520 | (1) |
|
|
|
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) |
|
|
|
523 | (1) |
|
Pd- or Ni-catalyzed Alkylation |
|
|
524 | (1) |
|
|
|
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) |
|
|
|
544 | (1) |
|
|
|
545 | (10) |
|
Enantioselective addition of organozinc compounds |
|
|
555 | (40) |
|
|
|
|
|
|
|
|
|
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) |
|
|
|
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) |
|
|
|
584 | (2) |
|
|
|
586 | (1) |
|
|
|
586 | (9) |
|
Rearrangements of organozinc compounds |
|
|
595 | (46) |
|
|
|
|
|
1,2-Metallate Rearrangements |
|
|
596 | (18) |
|
|
|
596 | (1) |
|
Reactions of 1,1-Dihalo Compounds with Triorganozincates |
|
|
596 | (1) |
|
|
|
597 | (1) |
|
|
|
598 | (2) |
|
|
|
600 | (2) |
|
1,2-Migrations with Loss of a Leaving Group Attached to a Remote Carbon |
|
|
602 | (1) |
|
Propargylic and homopropargylic substrates |
|
|
602 | (2) |
|
|
|
604 | (1) |
|
|
|
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) |
|
|
|
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) |
|
|
|
636 | (1) |
|
|
|
636 | (5) |
|
1,1-Bismetallated species |
|
|
641 | (44) |
|
|
|
|
|
641 | (1) |
|
Preparation of sp3-Geminated Organodizinc Reagents |
|
|
642 | (8) |
|
By Dihalomethane and Zinc |
|
|
643 | (2) |
|
|
|
645 | (1) |
|
By Heteroatom-substituted Dihaloalkane and Zinc |
|
|
646 | (1) |
|
|
|
647 | (3) |
|
Reaction of sp3-Geminated Organodizinc Reagents |
|
|
650 | (27) |
|
|
|
651 | (6) |
|
|
|
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) |
|
|
|
680 | (1) |
|
|
|
680 | (5) |
|
The chemistry of organozincate compounds |
|
|
685 | (28) |
|
|
|
|
|
685 | (1) |
|
|
|
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) |
|
|
|
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) |
|
|
|
706 | (1) |
|
|
|
707 | (2) |
|
|
|
709 | (1) |
|
|
|
709 | (4) |
|
Fluorinated organozinc reagents |
|
|
713 | (42) |
|
|
|
|
|
|
|
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) |
|
|
|
729 | (1) |
|
|
|
729 | (1) |
|
Preparation of functionalized CF3-containing compounds |
|
|
730 | (1) |
|
|
|
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) |
|
|
|
750 | (5) |
|
Electrochemical generation and reaction of zinc reagents |
|
|
755 | (42) |
|
|
|
|
|
|
|
|
|
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) |
|
|
|
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) |
|
|
|
769 | (1) |
|
Electrochemical Preparation of Organozinc Reagents Using Nickel Or Cobalt Catalysis |
|
|
769 | (25) |
|
|
|
769 | (2) |
|
Electrochemical Preparation of Organozinc Compounds using Nickel as Catalyst |
|
|
771 | (1) |
|
|
|
771 | (1) |
|
|
|
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) |
|
|
|
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) |
|
|
|
783 | (2) |
|
Electrosynthesis of aryl- or heteroarylzinc compounds |
|
|
785 | (1) |
|
In DMF/pyridine or CH3CN/pyridine as solvent |
|
|
786 | (3) |
|
|
|
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) |
|
|
|
794 | (1) |
|
|
|
795 | (2) |
|
The chemistry of zinc enolates |
|
|
797 | (66) |
|
|
|
|
|
General and Theoretical Aspects |
|
|
797 | (2) |
|
|
|
799 | (20) |
|
|
|
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) |
|
|
|
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) |
|
|
|
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) |
|
|
|
848 | (6) |
|
|
|
854 | (1) |
|
|
|
854 | (9) |
|
Carbozincation of alkenes and alkynes |
|
|
863 | (116) |
|
|
|
|
|
|
|
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) |
|
|
|
891 | (7) |
|
Transition metal-catalyzed reactions |
|
|
898 | (1) |
|
Intermolecular Allylzincation of Alkynes |
|
|
898 | (1) |
|
|
|
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) |
|
|
|
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) |
|
|
|
959 | (5) |
|
Intermolecular additions of zinc enolates to alkenes |
|
|
964 | (7) |
|
|
|
971 | (1) |
|
|
|
972 | (7) |
| Author index |
|
979 | (74) |
| Subject index |
|
1053 | |
Other versions by this Author
