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E-raamat: Cobalt Catalysis in Organic Synthesis: Methods and Reactions

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  • ISBN-13: 9783527814862
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Cobalt Catalysis in Organic Synthesis: Methods and ReactionsSuurem pilt
  • Formaat: EPUB+DRM
  • Ilmumisaeg: 17-Dec-2019
  • Kirjastus: Blackwell Verlag GmbH
  • Keel: eng
  • ISBN-13: 9783527814862
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Provides a much-needed account of the formidable "cobalt rush" in organic synthesis and catalysis

Over the past few decades, cobalt has turned into one of the most promising metals for use in catalytic reactions, with important applications in the efficient and selective synthesis of natural products, pharmaceuticals, and new materials.
Cobalt Catalysis in Organic Synthesis: Methods and Reactions provides a unique overview of cobalt-catalysed and -mediated reactions applied in modern organic synthesis. It covers a broad range of homogeneous reactions, like cobalt-catalysed hydrogenation, hydrofunctionalization, cycloaddition reactions, C-H functionalization, as well as radical and biomimetic reactions.
  • First comprehensive book on this rapidly evolving research area
  • Covers a broad range of homogeneous reactions, such as C-H activation, cross-coupling, synthesis of heterocyclic compounds (Pauson-Khand), and more
  • Chapters on low-valent cobalt complexes as catalysts in coupling reactions, and enantioselective cobalt-catalyzed transformations are also included
  • Can be used as a supplementary reader in courses of advanced organic synthesis and organometallic chemistry
Cobalt Catalysis in Organic Synthesis is an ideal book for graduates and researchers in academia and industry working in the field of synthetic organic chemistry, catalysis, organometallic chemistry, and natural product synthesis.
Preface xiii
1 Introduction to Cobalt Chemistry and Catalysis 1(24)
Marko Hapke
Gerhard Hilt
1.1 Introduction
1(3)
1.2 Organometallic Cobalt Chemistry, Reactions, and Connections to Catalysis
4(8)
1.2.1 Cobalt Compounds and Complexes of Oxidation States +3 to -1
4(6)
1.2.1.1 Co(III) Compounds
5(1)
1.2.1.2 Co(II) Compounds
5(2)
1.2.1.3 Co(I) Compounds
7(1)
1.2.1.4 Co(0) Compounds
8(1)
1.2.1.5 Co(-I) Compounds
9(1)
1.2.2 Bioorganometallic Cobalt Compounds
10(2)
1.3 Applications in Organic Synthesis and Catalytic Transformations
12(7)
1.4 Conclusion and Outlook
19(1)
Abbreviations
20(1)
References
20(5)
2 Homogeneous Cobalt-Catalysed Hydrogenation Reactions 25(42)
Kathrin Junge
Matthias Beller
2.1 Introduction
25(1)
2.2 Hydrogenation of C-C Multiple Bonds (Alkenes, Alkynes)
25(9)
2.3 Hydrogenation of Carbonyl Compounds (Ketones, Aldehydes, Carboxylic Acid Derivatives, CO2)
34(18)
2.3.1 Ketones and Aldehydes
34(5)
2.3.2 Carboxylic Acid Derivatives (Acids, Esters, Imides)
39(8)
2.3.3 Hydrogenation of Carbon Dioxide
47(5)
2.4 Hydrogenation of C-X Multiple Bonds (Imines, Nitriles)
52(6)
2.4.1 Nitrile Hydrogenation
52(3)
2.4.2 Imine Hydrogenation
55(1)
2.4.3 Hydrogenation of N-Heterocycles
56(2)
2.5 Summary and Conclusions
58(1)
2.6 Selected Experimental Procedures
59(1)
2.6.1 Synthesis of Cobalt Complex [ (PNHPcY)Co(CH2SiMe3)]BArF4 (8a)
59(1)
Abbreviations
60(1)
References
61(6)
3 Synthesis of C-C Bonds by Cobalt-Catalysed Hydrofunctionalisations 67(22)
Daniel K. Kim
Vy M. Dong
3.1 Introduction
67(1)
3.2 Cobalt-Catalysed C-C Bond Formations via Hydrofunctionalisation
67(16)
3.2.1 Hydroformylation
67(1)
3.2.2 Hydroacylation
68(6)
3.2.3 Hydrovinylation
74(4)
3.2.4 Hydroalkylation
78(2)
3.2.5 Hydrocyanation
80(1)
3.2.6 Hydrocarboxylation
81(2)
3.3 Summary and Conclusions
83(1)
Abbreviations
84(1)
References
85(4)
4 Cobalt-Catalysed C-H Functionalisation 89(74)
Naohiko Yoshikai
4.1 Introduction
89(2)
4.2 Low-valent Cobalt Catalysis
91(15)
4.2.1 C-H Functionalisation with In Situ-Reduced Cobalt Catalysts
91(14)
4.2.1.1 Hydroarylation of Alkynes and Alkenes
91(7)
4.2.1.2 C-H Functionalisation with Electrophiles
98(5)
4.2.1.3 C-H Functionalisation with Organometallic Reagents
103(1)
4.2.1.4 C-H Functionalisation via 1,4-Cobalt Migration
103(1)
4.2.1.5 Hydroacylation
103(2)
4.2.2 C-H Functionalisation with Pincer-Type Ligands and Related Well-Defined Cobalt Catalysts
105(1)
4.3 High-valent Cobalt Catalysis
106(40)
4.3.1 Chelation-Assisted C-H Functionalisation with Cp*CoIII Catalysts
106(24)
4.3.1.1 C-H Addition to Polar C=X Bonds
108(3)
4.3.1.2 Reaction with Alkynes, Alkenes, and Allenes
111(10)
4.3.1.3 Reaction with Formal Nitrene or Carbene Precursors
121(5)
4.3.1.4 Reaction with E-X-type Electrophiles
126(2)
4.3.1.5 Miscellaneous
128(2)
4.3.2 Bidentate Chelation-Assisted C-H Functionalisation with CoIII Catalysts
130(16)
4.3.2.1 Reaction with Alkynes, Alkenes, and Allenes
131(8)
4.3.2.2 Dehydrogenative Cross-coupling Reactions
139(4)
4.3.2.3 Carbonylation and Related Transformations
143(1)
4.3.2.4 Miscellaneous Transformations
144(2)
4.3.3 Miscellaneous
146(1)
4.4 Summary and Outlook
146(4)
Abbreviations
150(1)
References
151(12)
5 Low-valent Cobalt Complexes in C-X Coupling and Related Reactions 163(44)
Celine Dorval
Corinne Gosmini
5.1 Introduction
163(1)
5.2 Cobalt-Catalysed Coupling Reactions with Stoichiometric Organometallic Reagents
163(29)
5.2.1 Cobalt-Catalysed Coupling Reactions with Grignard Reagents
163(16)
5.2.1.1 Csp2-Csp2 Bond Formation
164(4)
5.2.1.2 Csp2-Csp3 Bond Formation
168(5)
5.2.1.3 Csp-Csp2 Bond Formation
173(1)
5.2.1.4 Csp-Csp3 Bond Formation
173(2)
5.2.1.5 Csp3-Csp3 Bond Formation
175(4)
5.2.2 Cobalt-Catalysed Coupling Reactions with Organozinc Reagents
179(8)
5.2.2.1 Csp-Csp2/Csp-Csp3 Bond Formation
179(2)
5.2.2.2 Csp2-Csp2 Bond Formation
181(2)
5.2.2.3 Csp2-Csp3 Bond Formation
183(3)
5.2.2.4 Csp2-CN Bond Formation
186(1)
5.2.2.5 Csp2-CO Bond Formation
186(1)
5.2.3 Carbon-Heteroatom Bond Formation
187(6)
5.2.3.1 C-N Bond Formation
187(1)
5.2.3.2 C-B Bond Formation
188(1)
5.2.4 Cobalt-Catalysed Coupling Reactions with Organoboron Reagents
188(4)
5.3 Cobalt-Catalysed Coupling Reactions with Organomanganese Reagents
192(1)
5.4 Cobalt-Catalysed Coupling Reactions with Copper Reagents
192(1)
5.5 Cobalt-Catalysed Reductive Cross-coupling Reactions
193(6)
5.5.1 Csp2-Csp2 Bond Formation
193(3)
5.5.2 Csp2-Csp3 Bond Formation
196(1)
5.5.3 Couplings with Benzylic Compounds
196(1)
5.5.4 Couplings with Allylic Acetates
197(1)
5.5.5 Csp3-Csp3 Carbon Bond Forming Reactions
197(2)
5.6 Overview and Perspectives
199(1)
5.7 Abbreviations
200(1)
References
201(6)
6 Ionic and Radical Reactions of It-Bonded Cobalt Complexes 207(28)
Gagik G. Melikyan
Elen Artashyan
6.1 Introduction
207(2)
6.2 Cobalt-Alkyne Complexes: Electrophilic Reactions
209(8)
6.2.1 Intramolecular Diels-Alder Reactions
210(1)
6.2.2 Assembling Tricyclic Ring Systems
211(1)
6.2.3 Assembling Bicyclic Ring Systems: Decalines
212(1)
6.2.4 Assembling Heterocyclic Ring Systems: Benzopyrans
212(1)
6.2.5 Synthesis of Enediynes
213(1)
6.2.6 Assembling Strained Ring Systems
213(2)
6.2.7 Assembling Natural Carbon Skeletons
215(2)
6.3 Cobalt-Alkyne Complexes: Radical Reactions
217(9)
6.4 Cobalt-1,3-enyne Complexes: Electrophilic Reactions
226(2)
6.5 Cobalt-1,3-enyne Complexes: Radical Reactions
228(1)
6.6 Prospects
228(2)
Abbreviations
230(1)
References
230(5)
7 Cobalt-Catalysed Cycloaddition Reactions 235(24)
Gerhard Hilt
7.1 Introduction
235(1)
7.2 Four-Membered Carbocyclic Ring Formation Reactions
235(5)
7.2.1 [ 2+2] Cycloaddition of Two Alkenes
235(2)
7.2.2 [ 2+2] Cycloaddition of an Alkene and an Alkyne
237(1)
7.2.3 [ 2+2] Cycloaddition of Two Alkynes
238(2)
7.3 Six-Membered Ring Formation Reactions
240(10)
7.3.1 Cobalt-Catalysed Diels-Alder Reactions
240(8)
7.3.2 Cobalt-Catalysed [ 2+2+2] Cycloaddition Reactions Other than Cyclotrimerisation of Alkynes
248(1)
7.3.3 Cobalt-Catalysed Benzannulation Reactions
249(1)
7.4 Synthesis of Larger Carbocyclic Ring Systems
250(3)
7.4.1 [ 3+2+2] and [ 5+2] Cycloaddition Reaction
250(1)
7.4.2 [ 6+2] Cycloaddition Reaction
251(2)
7.5 Conclusions
253(2)
Abbreviations
255(1)
References
255(4)
8 Recent Advances in the Pauson-Khand Reaction 259(28)
David M. Lindsay
William J. Kerr
8.1 Introduction
259(1)
8.2 Advances in the Pauson-Khand Reaction
259(10)
8.2.1 New Methods to Promote the Pauson-Khand Reaction
259(5)
8.2.1.1 Flow Chemistry Applications of the Pauson-Khand Reaction
260(1)
8.2.1.2 New Promoters
261(3)
8.2.2 Novel Substrates
264(12)
8.2.2.1 Maleimides as Alkene Partners
264(1)
8.2.2.2 Novel Enyne Substrates
265(3)
8.2.2.3 Strained Reaction Partners
268(1)
8.3 Asymmetric Pauson-Khand Reaction
269(4)
8.4 Mechanistic and Theoretical Studies
273(3)
8.5 Total Synthesis
276(4)
8.5.1 Synthesis of (+)-Ingenol
276(1)
8.5.2 Towards Retigeranic Acid A
277(1)
8.5.3 The Total Synthesis of Astellatol
278(1)
8.5.4 The Total Synthesis of 2-epi-α-Cedrene-3-one
279(1)
8.6 Summary and Conclusions
280(1)
8.7 Practical Procedures for Stoichiometric and Substoichiometric Pauson-Khand Reactions
281(1)
Abbreviations
282(1)
References
283(4)
9 Cobalt-Catalysed [ 2+2+2] Cycloadditions 287(50)
Tim Gleisel
Marko Hapke
9.1 Introduction
287(1)
9.2 Reaction Mechanisms of Cobalt-Catalysed Cyclotrimerisations
288(4)
9.3 Cobalt-Based Catalysts and Catalytic Systems
292(4)
9.4 CpCo-Based Cyclisations
296(6)
9.4.1 Carbocyclic Compounds
296(2)
9.4.2 Heterocyclic Compounds
298(4)
9.5 Non-CpCo-Based Cobalt-Catalysed Cyclisations
302(11)
9.5.1 Co2(CO)8-Mediated Cyclisations of Carbocyclic Compounds
302(2)
9.5.2 In Situ-Generated Catalysts and Precatalysts in Carbocyclisations of Alkynes
304(5)
9.5.3 In Situ-Generated Catalysts in the Cyclisation of Alkynes to Heterocyclic Compounds
309(4)
9.6 Cobalt-Mediated Asymmetric [ 2+2+2] Cycloadditions
313(4)
9.7 Cobalt-Mediated Cyclisations in Natural Product Synthesis
317(5)
9.8 Novel Developments of Cobalt-Mediated Cycloaddition Catalysis
322(4)
9.9 Summary and Outlook
326(1)
9.10 Selected Experimental Procedures
327(1)
9.10.1 Synthesis of [ CpCo(CO)(trans-MeO2CCH=CHCO2Me)] (PCAT5)
327(1)
9.10.2 Synthesis of [ CpCo(CO){P(OEt)3}] and [ CpCo(trans-MeO2CCH=CHCO2Me)(P(OEt)3}] (PCAT8)
327(1)
Abbreviations
328(2)
References
330(7)
10 Enantioselective Cobalt-Catalysed Transformations 337(80)
H. Pellissier
10.1 Introduction
337(1)
10.2 Synthesis of Chiral Acyclic Compounds Through Enantioselective Cobalt-Catalysed Reactions
338(32)
10.2.1 Michael and (Nitro)-Aldol Reactions
338(8)
10.2.1.1 Michael Reactions
338(4)
10.2.1.2 (Nitro)-Aldol Reactions
342(4)
10.2.2 Reduction Reactions
346(7)
10.2.2.1 Reductions of Carbonyl Compounds and Derivatives
346(3)
10.2.2.2 Reductions of Alkenes
349(4)
10.2.3 Ring-Opening Reactions
353(5)
10.2.3.1 Hydrolytic Ring-Openings of Epoxides
353(3)
10.2.3.2 Ring-Openings of Epoxides by Nucleophiles Other than Water
356(2)
10.2.4 Hydrovinylation and Hydroboration Reactions
358(5)
10.2.4.1 Hydrovinylations
358(3)
10.2.4.2 Hydroborations
361(2)
10.2.5 Cross-coupling Reactions
363(3)
10.2.6 Miscellaneous Reactions
366(4)
10.3 Enantioselective Cobalt-Catalysed Cyclisation Reactions
370(25)
10.3.1 [ 2+1] Cycloadditions
370(9)
10.3.2 Miscellaneous Cycloadditions
379(7)
10.3.2.1 (Hetero)-Diels-Alder Cycloadditions
379(1)
10.3.2.2 1,3-Dipolar Cycloadditions
380(3)
10.3.2.3 Other Cycloadditions
383(3)
10.3.3 Cyclisations Through Domino Reactions
386(4)
10.3.4 Miscellaneous Cyclisations
390(5)
10.4 Conclusions
395(1)
Abbreviations
396(1)
References
397(20)
11 Cobalt Radical Chemistry in Synthesis and Biomimetic Reactions (Including Vitamin B12) 417(36)
Michal Ociepa
Dorota Gryko
11.1 Introduction
417(1)
11.2 Cobalt-Mediated Reactions of Carbon-Centred Radicals
417(23)
11.2.1 Homocoupling Reactions
418(2)
11.2.2 Cross-coupling Reactions
420(3)
11.2.3 Additions to Alkenes and Alkynes
423(2)
11.2.4 Cyclisation Reactions
425(4)
11.2.5 Dehalogenation
429(2)
11.2.6 Oxidation
431(2)
11.2.7 Acylation
433(2)
11.2.8 Applications of Cobalt Complexes in Photoredox Catalysis
435(3)
11.2.9 Miscellaneous Reactions
438(2)
11.3 Cobalt-Mediated Reactions of Heteroatom-Centred Radicals
440(2)
11.3.1 Nitrogen-Centred Radicals
440(1)
11.3.2 Other Types of Radicals
441(1)
11.4 Overview and Conclusion
442(1)
11.5 Experimental Section
443(2)
11.5.1 Synthesis of Chloro(pyridine)cobaloxime Co(dmgH)2Cl(py) (116)
443(1)
11.5.2 Synthesis of Aqua(cyano)heptamethyl Cobyrinate (56b) - Hydrophobic Vitamin B12 Model
444(1)
11.5.3 General Procedure for Synthesis of Co(II)(salen) and Co(III)(salen) Complexes
445(1)
Abbreviations
445(1)
References
446(7)
Index 453
Marko Hapke is the Chair of Catalysis at the Johannes Kepler University in Linz, Austria, and also a group leader at the Leibniz Institute of Catalysis e.V. at the University of Rostock, Germany. His research centers on the development of novel cobalt catalysts for [ 2+2+2] cycloaddition reactions and the understanding of factors determinating reactivity and selectivity.

Gerhard Hilt is Full Professor at the Carl con Ossietzky University in Oldenburg, Germany. His research interests are applications of electron-transfer-activated transition-metal complexes in organic synthesis, quantification of Lewis acidities, organic electrochemistry, and surface-assisted transformations.
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