Muutke küpsiste eelistusi

E-raamat: Silver in Organic Chemistry [Wiley Online]

Edited by (University of Missouri, Columbia, USA), Foreword by
  • Formaat: 422 pages
  • Ilmumisaeg: 30-Jul-2010
  • Kirjastus: John Wiley & Sons Inc
  • ISBN-10: 470597526
  • ISBN-13: 9780470597521
Teised raamatud teemal:
  • Wiley Online
  • Hind: 140,62 €*
  • * hind, mis tagab piiramatu üheaegsete kasutajate arvuga ligipääsu piiramatuks ajaks
Silver in Organic ChemistrySuurem pilt
  • Formaat: 422 pages
  • Ilmumisaeg: 30-Jul-2010
  • Kirjastus: John Wiley & Sons Inc
  • ISBN-10: 470597526
  • ISBN-13: 9780470597521
Teised raamatud teemal:
Wiley Online e-raamatudRohkem infot Wiley Online kohta
Raamatu kodulehekülg: https://onlinelibrary.wiley.com/doi/book/10.1002/9780470597521
"The book will provide a resource for people wishing to do chemistry with silver cations, an area that stands in the shadow of gold chemistry but is quite powerful and ultimately less expensive"--

Provided by publisher.

With more sophisticated catalytic methodologies fueling a resurgence in the study of cation-based chemistry, gold and platinum have stepped to the fore as the unique agents used to create new chemical reactions. Although these metals have become a primary focus of researchers in the field, another coinage metal that is often overlooked---but is as powerful as the others---is silver, a far less costly alternative to gold and platinum in aiding the development of new reactions.

Making a strong case for the use of silver as a catalyst and structural element in organometal constructs, this authoritative book is the first to exlore the benefits of using silver in organic chemistry by taking a close look at silver's unique reactivity and structural characteristics for the development of new methods and materials. Silver in Organic Chemistry is

Silver in Organic Chemistry promotes further scientific discussion by offering important new ways to examine the future possibilities of an emerging field. By elevating the importance of silver chemistry, this thought-provoking guide illustrates how this versatile metal can become an increasingly significant player in opening the door to new catalytic organic reactions and new organometal materials.



The first authoritative book on using silver cations in organic chemistry—for catalysis and more!

With more sophisticated catalytic methodologies fueling a resurgence in the study of cation-based chemistry, gold and platinum have stepped to the fore as the unique agents used to create new chemical reactions. Although these metals have become a primary focus of researchers in the field, another coinage metal that is often overlooked—but is as powerful as the others—is silver, a far less costly alternative to gold and platinum in aiding the development of new reactions.

Making a strong case for the use of silver as a catalyst and structural element in organometal constructs, this authoritative book is the first to explore the benefits of using silver in organic chemistry by taking a close look at silver's unique reactivity and structural characteristics for the development of new methods and materials. Silver in Organic Chemistry is:

  • The first book to address catalysis using silver, whose use in organic chemistry is on the verge of exploding

  • A resource for researchers wishing to do chemistry with silver cations,an area that stands in the shadow of gold chemistry, but still glistens, demonstrating that all that glitters is not gold—sometimes it's silver!

  • A guide for "first attempts" in working with silver cations

  • Edited by a very well-respected, highly visible authority in this field

Silver in Organic Chemistry promotes further scientific discussion by offering important new ways to examine the future possibilities of an emerging field. By elevating the importance of silver chemistry, this thought-provoking guide illustrates how this versatile metal can become an increasingly significant player in opening the door to new catalytic organic reactions and new organometal materials.

Muu info

Commended for PROSE (Chemistry/Physics) 2010.
Foreword xv
Preface xvii
Contributors xix
1 Silver Alkyls, Alkenyls, Aryls, and Alkynyls in Organic Synthesis
1(42)
Rebecca H. Pouwer
Craig M. Williams
1.1 Introduction
2(1)
1.2 Csp3-Ag
2(8)
1.2.1 Synthesis, Stability, and Reactivity of Alkylsilver Compounds
2(5)
1.2.2 Synthesis and Stability of Perfluoroalkylsilver Compounds
7(2)
1.2.3 Reactivity of Perfluoroalkylsilver Compounds
9(1)
1.3 Csp2-Ag
10(8)
1.3.1 Synthesis and Stability of Arylsilver Compounds
10(1)
1.3.2 Reactivity of Arylsilver Compounds
11(1)
1.3.3 Synthesis and Stability of Perfluoroarylsilver Compounds
12(1)
1.3.4 Reactivity of Perfluoroarylsilver Compounds
13(1)
1.3.5 Synthesis, Stability, and Reactivity of Alkenylsilver Compounds
13(2)
1.3.6 Synthesis and Reactivity of Allenylsilver Compounds
15(1)
1.3.7 Synthesis of Perfluoroalkenylsilver Compounds
16(1)
1.3.8 Reactivity of Perfluoroalkenylsilver Compounds
17(1)
1.3.9 Synthesis and Reactivity of Silver-Substituted Diazomethyl Compounds
17(1)
1.4 Csp-Ag
18(18)
1.4.1 Synthesis of Silver Acetylides
19(1)
1.4.2 Reactivity of Silver Acetylides
20(1)
1.4.2.1 Addition to Activated Carbonyls and Iminium Ions
20(4)
1.4.2.2 Nucleophilic Substitution of Activated Heteroaromatics
24(1)
1.4.2.3 Reaction with Alkyl Halides
25(2)
1.4.2.4 Coupling Reactions
27(3)
1.4.2.5 Reactions with Non-carbon Electrophiles
30(2)
1.4.2.6 Fragmentation
32(1)
1.4.2.7 Desilylation
32(4)
1.5 Conclusion
36(7)
References
37(6)
2 Cycloaddition Reactions
43(40)
Alex M. Szpilman
Erick M. Carreira
2.1 Introduction
44(1)
2.2 [ 2+2] Cycloadditions
44(2)
2.3 [ 3+2] Cycloadditions
46(27)
2.3.1 [ 3+2] Cycloadditions of Azomethine Ylides
47(1)
2.3.1.1 Discovery and Development of the Silver-Catalyzed [ 3+2] Cycloaddition of Azomethine Ylides
47(3)
2.3.1.2 Auxiliary-Based Asymmetric [ 3+2] Cycloadditions
50(8)
2.3.1.3 Catalytic Asymmetric [ 3+2] Cycloadditions
58(8)
2.3.1.4 Selected Applications and Extensions of Azomethine [ 3+2] Cycloadditions
66(5)
2.3.2 Other [ 3+2] Cycloadditions
71(2)
2.4 [ 3+3] Cycloadditions
73(1)
2.5 [ 4+2] Cycloadditions
74(4)
2.6 Concluding Remarks
78(5)
References
79(4)
3 Sigmatropic Rearrangements and Related Processes Promoted by Silver
83(34)
Jean-Marc Weibel
Aurelien Blanc
Patrick Pale
3.1 Introduction
84(1)
3.2 Wolff and Arndt-Eistert Rearrangements and Related Reactions
84(2)
3.3 Ring Rearrangements
86(9)
3.3.1 Halogenoamines
86(2)
3.3.2 Cyclopropane Derivatives
88(4)
3.3.3 Cubane Derivatives
92(1)
3.3.4 Halogenocyclopropane Derivatives
93(2)
3.4 [ 3,3]-Sigmatropic Rearrangements
95(12)
3.4.1 With Acyl as Migrating Groups
95(3)
3.4.2 With Vinyl as Migrating Groups
98(3)
3.4.3 With Migrating Groups Analogous to Acyl
101(1)
3.4.4 [ 3,3]-Sigmatropic Rearrangement and Cyclization Cascades
102(5)
3.5 [ 2,3]-Sigmatropic Rearrangements
107(1)
3.6 [ 1,2]-Sigmatropic Rearrangements
108(5)
3.6.1 1,2-Aryl or Alkenyl Migration
108(2)
3.6.2 1,2-Alkyl Migration
110(1)
3.6.3 1,2- or 1,5-Alkyl Migration
110(1)
3.6.4 1,2 versus 3,3 Migrations
111(2)
3.7 Miscellaneous
113(1)
3.8 Conclusion
113(4)
References
114(3)
4 Silver(I)-Mediated Electrocyclic Processes
117(26)
Tina N. Grant
Frederick G. West
4.1 Introduction
117(4)
4.1.1 Ring-Opening Reactions of Halocyclopropanes
118(2)
4.1.2 Silver(I)-Assisted Ring-Opening Reactions
120(1)
4.2 Nucleophilic Trapping of Cationic Intermediates
121(11)
4.2.1 Solvolysis Reactions
121(3)
4.2.2 Intramolecular Trapping with Heteronucleophiles
124(3)
4.2.3 Diastereoselective Reactions
127(2)
4.2.4 Carbon-Carbon Bond Formation
129(3)
4.3 The Silver(I)-Promoted Nazarov Reaction
132(7)
4.3.1 Development and Initial Findings
133(2)
4.3.2 Interrupted Nazarov Reactions
135(4)
4.4 Concluding Remarks
139(4)
References
139(4)
5 Silver-Catalyzed Cycloisomerization Reactions
143(24)
Philippe Belmont
5.1 Introduction
143(1)
5.2 Cycloisomerization of C=O onto C=C=C
144(4)
5.3 Cycloisomerization of C=O onto C≡C
148(4)
5.4 Cycloisomerization of C=N onto C=C=C
152(1)
5.5 Cycloisomerization of C=N onto C≡C
153(4)
5.6 Ene---Yne Cycloisomerization: C=C onto C≡C
157(3)
5.7 Other Transformations
160(2)
5.8 Conclusion
162(5)
References
162(5)
6 Silver-Catalyzed Nitrene Transfer Reactions
167(16)
Zigang Li
David A. Capretto
Chuan He
6.1 Introduction
167(2)
6.2 Aziridination
169(3)
6.2.1 Chloramine-T as Nitrene Precursor
169(1)
6.2.2 Iminoiodanes as Nitrene Precursors
169(3)
6.2.3 Heterogenous Silver Catalysis
172(1)
6.3 Sulfide and Sulfoxide Imination
172(1)
6.4 Amidation
173(7)
6.4.1 Intramolecular Amidation
173(1)
6.4.2 Intermolecular Amination with Phenanthroline Ligands
174(3)
6.4.3 Intermolecular Amination Based on Pyrazolylborate Ligands
177(3)
6.5 Conclusion
180(3)
References
180(3)
7 Silver-Catalyzed Silylene Transfer
183(46)
Tom G. Driver
7.1 Introduction
183(1)
7.2 Reactivity and Attributes of Metal Silylenoids and Silylmetal Complexes
184(6)
7.2.1 Synthesis of Transition Metal Complexes of Silylenes
184(3)
7.2.2 Reactivity of Transition Metal Silylenoids
187(1)
7.2.3 Transition Metal Silylenoid Complex-Catalyzed Hydrosilation Reactions
187(2)
7.2.4 Transition Metal Silylenoid-Catalyzed Atom Transfer Reactions
189(1)
7.3 Silacyclopropanes as Important Synthetic Intermediates
190(2)
7.4 Silver-Mediated Transfer of Di-tert-Butylsilylene to Olefins
192(8)
7.5 Silver-Mediated Transfer of Di-tert-Butylsilylene to Acetylenes
200(7)
7.6 Silver-Mediated Transfer of Di-tert-Butylsilylene to Carbonyl Compounds
207(7)
7.7 Silver-Mediated Transfer of Di-tert-Butylsilylene to Imines
214(5)
7.8 Silver-Mediated Di-tert-Butylsilylene Insertion into C-O Bonds
219(2)
7.9 Conclusion
221(8)
References
222(7)
8 Silver Carbenoids
229(30)
Carl J. Lovely
8.1 Introduction
229(1)
8.2 Wolff Rearrangement
230(2)
8.3 Carbene Transfer Reactions to π Bonds
232(2)
8.3.1 Aziridination
232(1)
8.3.2 Cyclopropanation
233(1)
8.4 Formation and Reactions of Ylides
234(8)
8.4.1 C-Hal Addition-Rearrangement
234(7)
8.4.2 C-S Addition-Rearrangement
241(1)
8.5 C-H Insertion
242(1)
8.6 N-H Insertion
243(7)
8.7 Ring Expansion Reactions
250(1)
8.8 Intermediacy of Silver Carbenes
250(3)
8.9 Miscellaneous Reactions Involving Silver Carbenoids
253(1)
8.10 Summary
254(5)
Acknowledgments
255(1)
References
255(4)
9 Aldol and Related Processes
259(26)
Masanori Kawasaki
Hisashi Yamamoto
9.1 Introduction
259(1)
9.2 Allylation Reaction Using Allyltributyltin
260(4)
9.3 Allylation Reaction Using Allylsilanes
264(4)
9.4 Aldol Reaction Using Tin Enolates
268(3)
9.5 Aldol Reaction Using Silyl Enol Ethers
271(5)
9.6 Mannich Reaction
276(1)
9.7 Nitrosoaldol Reaction
277(4)
9.8 Aldol Reaction with Azodicarboxylate
281(1)
9.9 Conclusion
281(4)
References
282(3)
10 Coupling Reactions Promoted by Silver
285(44)
Jean-Marc Weibel
Aurelien Blanc
Patrick Pale
10.1 Introduction
286(1)
10.2 sp3-sp3 Coupling Reactions Promoted by Silver Salts
286(3)
10.3 sp3-sp2 Coupling Reactions Promoted by Silver Salts
289(1)
10.4 sp3-sp Coupling Reactions Promoted by Silver Salts
290(1)
10.5 sp2-sp2 Coupling Reactions Promoted by Silver Salts
291(19)
10.5.1 Homocoupling of Vinyl- or Arylsilver Species
292(1)
10.5.2 Organosilver Species as Nucleophilic Reagents
293(1)
10.5.3 Silver as a Lewis Acid Reagent
294(3)
10.5.4 Silver as a Halogen Scavenger
297(1)
10.5.4.1 Silver in Pd-Catalyzed Couplings
298(8)
10.5.4.2 Silver in PdII-Promoted Electrophilic Substitution of Arenes (C-H Activation)
306(3)
10.5.4.3 Silver as Reagent for Decarboxylative Coupling
309(1)
10.6 sp2-sp Coupling Reactions Promoted by Silver Salts
310(12)
10.6.1 Organosilver Species as Nucleophilic Reagents
311(3)
10.6.2 Organosilver Species in Transmetallations
314(1)
10.6.3 Silver as a Lewis Acid Reagent
315(1)
10.6.4 Organosilver Species as Intermediates in Catalyzed Enyne or Arylyne Synthesis
316(6)
10.7 sp-sp Coupling Reactions Promoted by Silver Salts
322(1)
10.8 Conclusion
323(6)
References
324(5)
11 Supramolecular Chemistry of Silver
329(28)
Wei-Yin Sun
Zheng-Shuai Bai
Jin-Quan Yu
11.1 Introduction
329(1)
11.2 Cage-Like Complexes
330(7)
11.3 Tube-Like Compounds
337(2)
11.4 Polycatenanes with Silver(I)
339(3)
11.5 Polyrotaxanes with Silver(I)
342(3)
11.6 Silver(I) Coordination Polymers with Specific Topology
345(5)
11.7 Conclusion
350(7)
Acknowledgments
352(1)
References
352(5)
12 A Critical Comparison: Copper, Silver, and Gold
357(24)
A. Stephen
K. Hashmi
12.1 Introduction
358(1)
12.2 Reactions Catalyzed by Copper, Silver, or Gold
358(10)
12.2.1 Aldehyde-Alkyne-Amine Coupling
358(2)
12.2.2 Carbene Insertion Reactions
360(1)
12.2.3 In Silico Comparison of Organocopper(I), Organosilver(I), and Organogold(I) -Ate Compounds
361(1)
12.2.4 Cyclization of ortho-alkynylbenzaldehydes
362(1)
12.2.5 Allenyl Ketones: The Cycloisomerization to Furans
362(2)
12.2.6 A Thiol in the Substrate: The Cyclization of α-Thioallenes
364(1)
12.2.7 Furans by Propargyl Claisen Reaction
365(1)
12.2.8 Tandem Cyclization/Pinacol Rearrangement
366(1)
12.2.9 Furanones by Domino Heterocyclization/1,2 Shift
366(2)
12.2.10 Conia-ene Reaction
368(1)
12.3 Reactions Catalyzed by Silver or Gold
368(6)
12.3.1 Cyclization of N-Propargylcarboxamides
368(1)
12.3.2 Dake's Pyrrole Synthesis
369(1)
12.3.3 Combination with Organocatalysis
369(1)
12.3.4 Vinylallenes Deliver Cyclopentadienes
370(1)
12.3.5 α-Pyrones by a Cascade Reaction
371(1)
12.3.6 Dihydrofurans from Propargyl Esters
371(1)
12.3.7 Methylene Butyrolactones by Addition of Carboxylates to Alkynes
372(1)
12.3.8 Hydroarylation of Allenes
373(1)
12.3.9 Different Products by Silver and Gold Catalysts
373(1)
12.3.9.1 The Epoxide-Alkyne Reaction
373(1)
12.3.9.2 The Carbonyl-Alkyne Reaction
374(1)
12.4 Reactions Catalyzed by Copper or Silver
374(2)
12.4.1 General Trends
374(1)
12.4.2 Pyrroles by Hydroamination
374(1)
12.4.3 Copper/Silver Cocatalysis
375(1)
12.4.4 Carbonylations
375(1)
12.5 Conclusion
376(5)
References
376(5)
Index 381
MICHAEL HARMATA holds the academic position of Norman Rabjohn Distinguished Professor of Chemistry at the University of Missouri-Columbia. He has published extensively in his field and has been chair of the Gordon Research Conference on Organic Reactions and Processes (2000) and has served as an invited speaker at many U.S. and international universities and conferences, including the International Symposium on Molecular Recognition and Inclusion, the International Congress on Heterocyclic Chemistry, and the International IUPAC Conference on Organic Synthesis. Dr. Harmata has also served on the editorial board of Mini-Reviews in Organic Chemistry and Chemtracts Organic Chemistry. He is the Editor of Elseviers book series, Strategies and Tactics in Organic Synthesis, and editor of Springers Organic Mechanisms.
Püsilink: https://www.kriso.ee/db/9780470597521_pe.html
Märksõnad: