Silver in Organic Chemistry
Herausgeber: Harmata, Michael
Silver in Organic Chemistry
Herausgeber: Harmata, Michael
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This book serves as a resource for researchers 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. It contains experimental procedures that serve as a useful guide for first attempts in working with silver cations. Written by a well-respected, highly visible authority in the field, this is the first book addressing silver cation catalysis in organic chemistry, providing a much-needed resource on mechanisms, methods, advantages, and efficiencies in organometallic synthesis.
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This book serves as a resource for researchers 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. It contains experimental procedures that serve as a useful guide for first attempts in working with silver cations. Written by a well-respected, highly visible authority in the field, this is the first book addressing silver cation catalysis in organic chemistry, providing a much-needed resource on mechanisms, methods, advantages, and efficiencies in organometallic synthesis.
Produktdetails
- Produktdetails
- Verlag: John Wiley & Sons / Wiley
- Seitenzahl: 422
- Erscheinungstermin: 7. September 2010
- Englisch
- Abmessung: 240mm x 161mm x 27mm
- Gewicht: 800g
- ISBN-13: 9780470466117
- ISBN-10: 0470466111
- Artikelnr.: 28707965
- Verlag: John Wiley & Sons / Wiley
- Seitenzahl: 422
- Erscheinungstermin: 7. September 2010
- Englisch
- Abmessung: 240mm x 161mm x 27mm
- Gewicht: 800g
- ISBN-13: 9780470466117
- ISBN-10: 0470466111
- Artikelnr.: 28707965
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 Elsevier's book series, Strategies and Tactics in Organic Synthesis, and editor of Springer's Organic Mechanisms.
Foreword. Preface. Contributors. 1 Silver Alkyls, Alkenyls, Aryls, and
Alkynyls in Organic Synthesis (Rebecca H. Pouwer and Craig M. Williams).
1.1 Introduction. 1.2 Csp3-Ag. 1.3 Csp2-Ag. 1.4 Csp-Ag. 1.5 Conclusion.
References. 2 Cycloaddition Reactions (Alex M. Szpilman and Erick M.
Carreira). 2.1 Introduction. 2.2 [2+2] Cycloadditions. 2.3 [3+2]
Cycloadditions. 2.4 [3+3] Cycloadditions. 2.5 [4+2] Cycloadditions. 2.6
Concluding Remarks. References. 3 Sigmatropic Rearrangements and Related
Processes Promoted by Silver (Jean-Marc Weibel, Aureelien Blanc, and
Patrick Pale). 3.1 Introduction. 3.2 Wolff and Arndt-Eistert Rearrangements
and Related Reactions. 3.3 Ring Rearrangements. 3.4 [3,3]-Sigmatropic
Rearrangements. 3.5 [2,3]-Sigmatropic Rearrangements. 3.6 [1,2]-Sigmatropic
Rearrangements. 3.7 Miscellaneous. 3.8 Conclusion. References. 4
Silver(I)-Mediated Electrocyclic Processes (Tina N. Grant and Frederick G.
West). 4.1 Introduction. 4.2 Nucleophilic Trapping of Cationic
Intermediates. 4.3 The Silver(I)-Promoted Nazarov Reaction. 4.4 Concluding
Remarks. References. 5 Silver-Catalyzed Cycloisomerization Reactions
(Philippe Belmont). 5.1 Introduction. 5.2 Cycloisomerization of C=O onto
C=C=C. 5.3 Cycloisomerization of C=O onto C=C. 5.4 Cycloisomerization of
C=N onto C=C=C. 5.5 Cycloisomerization of C=N onto C=C. 5.6 Ene-Yne
Cycloisomerization: C=C onto C=C. 5.7 Other Transformations. 5.8
Conclusion. References. 6 Silver-Catalyzed Nitrene Transfer Reactions
(Zigang Li, David A. Capretto, and Chuan He). 6.1 Introduction. 6.2
Aziridination. 6.3 Sulfide and Sulfoxide Imination. 6.4 Amidation. 6.5
Conclusion. References. 7 Silver-Catalyzed Silylene Transfer (Tom G.
Driver). 7.1 Introduction. 7.2 Reactivity and Attributes of Metal
Silylenoids and Silylmetal Complexes. 7.3 Silacyclopropanes as Important
Synthetic Intermediates. 7.4 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Olefins. 7.5 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Acetylenes. 7.6 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Carbonyl Compounds. 7.7 Silver-Mediated Transfer
of Di-tert-Butylsilylene to Imines. 7.8 Silver-Mediated
Di-tert-Butylsilylene Insertion into C--O Bonds. 7.9 Conclusion.
References. 8 Silver Carbenoids (Carl J. Lovely). 8.1 Introduction. 8.2
Wolff Rearrangement. 8.3 Carbene Transfer Reactions to p Bonds. 8.4
Formation and Reactions of Ylides. 8.5 C--H Insertion. 8.6 N--H Insertion.
8.7 Ring Expansion Reactions. 8.8 Intermediacy of Silver Carbenes. 8.9
Miscellaneous Reactions Involving Silver Carbenoids. 8.10 Summary.
Acknowledgments. References. 9 Aldol and Related Processes (Masanori
Kawasaki and Hisashi Yamamoto). 9.1 Introduction. 9.2 Allylation Reaction
Using Allyltributyltin. 9.3 Allylation Reaction Using Allylsilanes. 9.4
Aldol Reaction Using Tin Enolates. 9.5 Aldol Reaction Using Silyl Enol
Ethers. 9.6 Mannich Reaction. 9.7 Nitrosoaldol Reaction. 9.8 Aldol Reaction
with Azodicarboxylate. 9.9 Conclusion. References. 10 Coupling Reactions
Promoted by Silver (Jean-Marc Weibel, Aurelien Blanc, and Patrick Pale).
10.1 Introduction. 10.2 sp3-sp3 Coupling Reactions Promoted by Silver
Salts. 10.3 sp3-sp2 Coupling Reactions Promoted by Silver Salts. 10.4
sp3-sp Coupling Reactions Promoted by Silver Salts. 10.5 sp2-sp2 Coupling
Reactions Promoted by Silver Salts. 10.6 sp2-sp Coupling Reactions Promoted
by Silver Salts. 10.7 sp-sp Coupling Reactions Promoted by Silver Salts.
10.8 Conclusion. References. 11 Supramolecular Chemistry of Silver (Wei-Yin
Sun, Zheng-Shuai Bai, and Jin-Quan Yu). 11.1 Introduction. 11.2 Cage-Like
Complexes. 11.3 Tube-Like Compounds. 11.4 Polycatenanes with Silver(I).
11.5 Polyrotaxanes with Silver(I). 11.6 Silver(I) Coordination Polymers
with Specific Topology. 11.7 Conclusion. Acknowledgments. References. 12 A
Critical Comparison: Copper, Silver, and Gold (A. Stephen K. Hashmi). 12.1
Introduction. 12.2 Reactions Catalyzed by Copper, Silver, or Gold. 12.3
Reactions Catalyzed by Silver or Gold. 12.4 Reactions Catalyzed by Copper
or Silver. 12.5 Conclusion. References. Index.
Alkynyls in Organic Synthesis (Rebecca H. Pouwer and Craig M. Williams).
1.1 Introduction. 1.2 Csp3-Ag. 1.3 Csp2-Ag. 1.4 Csp-Ag. 1.5 Conclusion.
References. 2 Cycloaddition Reactions (Alex M. Szpilman and Erick M.
Carreira). 2.1 Introduction. 2.2 [2+2] Cycloadditions. 2.3 [3+2]
Cycloadditions. 2.4 [3+3] Cycloadditions. 2.5 [4+2] Cycloadditions. 2.6
Concluding Remarks. References. 3 Sigmatropic Rearrangements and Related
Processes Promoted by Silver (Jean-Marc Weibel, Aureelien Blanc, and
Patrick Pale). 3.1 Introduction. 3.2 Wolff and Arndt-Eistert Rearrangements
and Related Reactions. 3.3 Ring Rearrangements. 3.4 [3,3]-Sigmatropic
Rearrangements. 3.5 [2,3]-Sigmatropic Rearrangements. 3.6 [1,2]-Sigmatropic
Rearrangements. 3.7 Miscellaneous. 3.8 Conclusion. References. 4
Silver(I)-Mediated Electrocyclic Processes (Tina N. Grant and Frederick G.
West). 4.1 Introduction. 4.2 Nucleophilic Trapping of Cationic
Intermediates. 4.3 The Silver(I)-Promoted Nazarov Reaction. 4.4 Concluding
Remarks. References. 5 Silver-Catalyzed Cycloisomerization Reactions
(Philippe Belmont). 5.1 Introduction. 5.2 Cycloisomerization of C=O onto
C=C=C. 5.3 Cycloisomerization of C=O onto C=C. 5.4 Cycloisomerization of
C=N onto C=C=C. 5.5 Cycloisomerization of C=N onto C=C. 5.6 Ene-Yne
Cycloisomerization: C=C onto C=C. 5.7 Other Transformations. 5.8
Conclusion. References. 6 Silver-Catalyzed Nitrene Transfer Reactions
(Zigang Li, David A. Capretto, and Chuan He). 6.1 Introduction. 6.2
Aziridination. 6.3 Sulfide and Sulfoxide Imination. 6.4 Amidation. 6.5
Conclusion. References. 7 Silver-Catalyzed Silylene Transfer (Tom G.
Driver). 7.1 Introduction. 7.2 Reactivity and Attributes of Metal
Silylenoids and Silylmetal Complexes. 7.3 Silacyclopropanes as Important
Synthetic Intermediates. 7.4 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Olefins. 7.5 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Acetylenes. 7.6 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Carbonyl Compounds. 7.7 Silver-Mediated Transfer
of Di-tert-Butylsilylene to Imines. 7.8 Silver-Mediated
Di-tert-Butylsilylene Insertion into C--O Bonds. 7.9 Conclusion.
References. 8 Silver Carbenoids (Carl J. Lovely). 8.1 Introduction. 8.2
Wolff Rearrangement. 8.3 Carbene Transfer Reactions to p Bonds. 8.4
Formation and Reactions of Ylides. 8.5 C--H Insertion. 8.6 N--H Insertion.
8.7 Ring Expansion Reactions. 8.8 Intermediacy of Silver Carbenes. 8.9
Miscellaneous Reactions Involving Silver Carbenoids. 8.10 Summary.
Acknowledgments. References. 9 Aldol and Related Processes (Masanori
Kawasaki and Hisashi Yamamoto). 9.1 Introduction. 9.2 Allylation Reaction
Using Allyltributyltin. 9.3 Allylation Reaction Using Allylsilanes. 9.4
Aldol Reaction Using Tin Enolates. 9.5 Aldol Reaction Using Silyl Enol
Ethers. 9.6 Mannich Reaction. 9.7 Nitrosoaldol Reaction. 9.8 Aldol Reaction
with Azodicarboxylate. 9.9 Conclusion. References. 10 Coupling Reactions
Promoted by Silver (Jean-Marc Weibel, Aurelien Blanc, and Patrick Pale).
10.1 Introduction. 10.2 sp3-sp3 Coupling Reactions Promoted by Silver
Salts. 10.3 sp3-sp2 Coupling Reactions Promoted by Silver Salts. 10.4
sp3-sp Coupling Reactions Promoted by Silver Salts. 10.5 sp2-sp2 Coupling
Reactions Promoted by Silver Salts. 10.6 sp2-sp Coupling Reactions Promoted
by Silver Salts. 10.7 sp-sp Coupling Reactions Promoted by Silver Salts.
10.8 Conclusion. References. 11 Supramolecular Chemistry of Silver (Wei-Yin
Sun, Zheng-Shuai Bai, and Jin-Quan Yu). 11.1 Introduction. 11.2 Cage-Like
Complexes. 11.3 Tube-Like Compounds. 11.4 Polycatenanes with Silver(I).
11.5 Polyrotaxanes with Silver(I). 11.6 Silver(I) Coordination Polymers
with Specific Topology. 11.7 Conclusion. Acknowledgments. References. 12 A
Critical Comparison: Copper, Silver, and Gold (A. Stephen K. Hashmi). 12.1
Introduction. 12.2 Reactions Catalyzed by Copper, Silver, or Gold. 12.3
Reactions Catalyzed by Silver or Gold. 12.4 Reactions Catalyzed by Copper
or Silver. 12.5 Conclusion. References. Index.
Foreword. Preface. Contributors. 1 Silver Alkyls, Alkenyls, Aryls, and
Alkynyls in Organic Synthesis (Rebecca H. Pouwer and Craig M. Williams).
1.1 Introduction. 1.2 Csp3-Ag. 1.3 Csp2-Ag. 1.4 Csp-Ag. 1.5 Conclusion.
References. 2 Cycloaddition Reactions (Alex M. Szpilman and Erick M.
Carreira). 2.1 Introduction. 2.2 [2+2] Cycloadditions. 2.3 [3+2]
Cycloadditions. 2.4 [3+3] Cycloadditions. 2.5 [4+2] Cycloadditions. 2.6
Concluding Remarks. References. 3 Sigmatropic Rearrangements and Related
Processes Promoted by Silver (Jean-Marc Weibel, Aureelien Blanc, and
Patrick Pale). 3.1 Introduction. 3.2 Wolff and Arndt-Eistert Rearrangements
and Related Reactions. 3.3 Ring Rearrangements. 3.4 [3,3]-Sigmatropic
Rearrangements. 3.5 [2,3]-Sigmatropic Rearrangements. 3.6 [1,2]-Sigmatropic
Rearrangements. 3.7 Miscellaneous. 3.8 Conclusion. References. 4
Silver(I)-Mediated Electrocyclic Processes (Tina N. Grant and Frederick G.
West). 4.1 Introduction. 4.2 Nucleophilic Trapping of Cationic
Intermediates. 4.3 The Silver(I)-Promoted Nazarov Reaction. 4.4 Concluding
Remarks. References. 5 Silver-Catalyzed Cycloisomerization Reactions
(Philippe Belmont). 5.1 Introduction. 5.2 Cycloisomerization of C=O onto
C=C=C. 5.3 Cycloisomerization of C=O onto C=C. 5.4 Cycloisomerization of
C=N onto C=C=C. 5.5 Cycloisomerization of C=N onto C=C. 5.6 Ene-Yne
Cycloisomerization: C=C onto C=C. 5.7 Other Transformations. 5.8
Conclusion. References. 6 Silver-Catalyzed Nitrene Transfer Reactions
(Zigang Li, David A. Capretto, and Chuan He). 6.1 Introduction. 6.2
Aziridination. 6.3 Sulfide and Sulfoxide Imination. 6.4 Amidation. 6.5
Conclusion. References. 7 Silver-Catalyzed Silylene Transfer (Tom G.
Driver). 7.1 Introduction. 7.2 Reactivity and Attributes of Metal
Silylenoids and Silylmetal Complexes. 7.3 Silacyclopropanes as Important
Synthetic Intermediates. 7.4 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Olefins. 7.5 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Acetylenes. 7.6 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Carbonyl Compounds. 7.7 Silver-Mediated Transfer
of Di-tert-Butylsilylene to Imines. 7.8 Silver-Mediated
Di-tert-Butylsilylene Insertion into C--O Bonds. 7.9 Conclusion.
References. 8 Silver Carbenoids (Carl J. Lovely). 8.1 Introduction. 8.2
Wolff Rearrangement. 8.3 Carbene Transfer Reactions to p Bonds. 8.4
Formation and Reactions of Ylides. 8.5 C--H Insertion. 8.6 N--H Insertion.
8.7 Ring Expansion Reactions. 8.8 Intermediacy of Silver Carbenes. 8.9
Miscellaneous Reactions Involving Silver Carbenoids. 8.10 Summary.
Acknowledgments. References. 9 Aldol and Related Processes (Masanori
Kawasaki and Hisashi Yamamoto). 9.1 Introduction. 9.2 Allylation Reaction
Using Allyltributyltin. 9.3 Allylation Reaction Using Allylsilanes. 9.4
Aldol Reaction Using Tin Enolates. 9.5 Aldol Reaction Using Silyl Enol
Ethers. 9.6 Mannich Reaction. 9.7 Nitrosoaldol Reaction. 9.8 Aldol Reaction
with Azodicarboxylate. 9.9 Conclusion. References. 10 Coupling Reactions
Promoted by Silver (Jean-Marc Weibel, Aurelien Blanc, and Patrick Pale).
10.1 Introduction. 10.2 sp3-sp3 Coupling Reactions Promoted by Silver
Salts. 10.3 sp3-sp2 Coupling Reactions Promoted by Silver Salts. 10.4
sp3-sp Coupling Reactions Promoted by Silver Salts. 10.5 sp2-sp2 Coupling
Reactions Promoted by Silver Salts. 10.6 sp2-sp Coupling Reactions Promoted
by Silver Salts. 10.7 sp-sp Coupling Reactions Promoted by Silver Salts.
10.8 Conclusion. References. 11 Supramolecular Chemistry of Silver (Wei-Yin
Sun, Zheng-Shuai Bai, and Jin-Quan Yu). 11.1 Introduction. 11.2 Cage-Like
Complexes. 11.3 Tube-Like Compounds. 11.4 Polycatenanes with Silver(I).
11.5 Polyrotaxanes with Silver(I). 11.6 Silver(I) Coordination Polymers
with Specific Topology. 11.7 Conclusion. Acknowledgments. References. 12 A
Critical Comparison: Copper, Silver, and Gold (A. Stephen K. Hashmi). 12.1
Introduction. 12.2 Reactions Catalyzed by Copper, Silver, or Gold. 12.3
Reactions Catalyzed by Silver or Gold. 12.4 Reactions Catalyzed by Copper
or Silver. 12.5 Conclusion. References. Index.
Alkynyls in Organic Synthesis (Rebecca H. Pouwer and Craig M. Williams).
1.1 Introduction. 1.2 Csp3-Ag. 1.3 Csp2-Ag. 1.4 Csp-Ag. 1.5 Conclusion.
References. 2 Cycloaddition Reactions (Alex M. Szpilman and Erick M.
Carreira). 2.1 Introduction. 2.2 [2+2] Cycloadditions. 2.3 [3+2]
Cycloadditions. 2.4 [3+3] Cycloadditions. 2.5 [4+2] Cycloadditions. 2.6
Concluding Remarks. References. 3 Sigmatropic Rearrangements and Related
Processes Promoted by Silver (Jean-Marc Weibel, Aureelien Blanc, and
Patrick Pale). 3.1 Introduction. 3.2 Wolff and Arndt-Eistert Rearrangements
and Related Reactions. 3.3 Ring Rearrangements. 3.4 [3,3]-Sigmatropic
Rearrangements. 3.5 [2,3]-Sigmatropic Rearrangements. 3.6 [1,2]-Sigmatropic
Rearrangements. 3.7 Miscellaneous. 3.8 Conclusion. References. 4
Silver(I)-Mediated Electrocyclic Processes (Tina N. Grant and Frederick G.
West). 4.1 Introduction. 4.2 Nucleophilic Trapping of Cationic
Intermediates. 4.3 The Silver(I)-Promoted Nazarov Reaction. 4.4 Concluding
Remarks. References. 5 Silver-Catalyzed Cycloisomerization Reactions
(Philippe Belmont). 5.1 Introduction. 5.2 Cycloisomerization of C=O onto
C=C=C. 5.3 Cycloisomerization of C=O onto C=C. 5.4 Cycloisomerization of
C=N onto C=C=C. 5.5 Cycloisomerization of C=N onto C=C. 5.6 Ene-Yne
Cycloisomerization: C=C onto C=C. 5.7 Other Transformations. 5.8
Conclusion. References. 6 Silver-Catalyzed Nitrene Transfer Reactions
(Zigang Li, David A. Capretto, and Chuan He). 6.1 Introduction. 6.2
Aziridination. 6.3 Sulfide and Sulfoxide Imination. 6.4 Amidation. 6.5
Conclusion. References. 7 Silver-Catalyzed Silylene Transfer (Tom G.
Driver). 7.1 Introduction. 7.2 Reactivity and Attributes of Metal
Silylenoids and Silylmetal Complexes. 7.3 Silacyclopropanes as Important
Synthetic Intermediates. 7.4 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Olefins. 7.5 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Acetylenes. 7.6 Silver-Mediated Transfer of
Di-tert-Butylsilylene to Carbonyl Compounds. 7.7 Silver-Mediated Transfer
of Di-tert-Butylsilylene to Imines. 7.8 Silver-Mediated
Di-tert-Butylsilylene Insertion into C--O Bonds. 7.9 Conclusion.
References. 8 Silver Carbenoids (Carl J. Lovely). 8.1 Introduction. 8.2
Wolff Rearrangement. 8.3 Carbene Transfer Reactions to p Bonds. 8.4
Formation and Reactions of Ylides. 8.5 C--H Insertion. 8.6 N--H Insertion.
8.7 Ring Expansion Reactions. 8.8 Intermediacy of Silver Carbenes. 8.9
Miscellaneous Reactions Involving Silver Carbenoids. 8.10 Summary.
Acknowledgments. References. 9 Aldol and Related Processes (Masanori
Kawasaki and Hisashi Yamamoto). 9.1 Introduction. 9.2 Allylation Reaction
Using Allyltributyltin. 9.3 Allylation Reaction Using Allylsilanes. 9.4
Aldol Reaction Using Tin Enolates. 9.5 Aldol Reaction Using Silyl Enol
Ethers. 9.6 Mannich Reaction. 9.7 Nitrosoaldol Reaction. 9.8 Aldol Reaction
with Azodicarboxylate. 9.9 Conclusion. References. 10 Coupling Reactions
Promoted by Silver (Jean-Marc Weibel, Aurelien Blanc, and Patrick Pale).
10.1 Introduction. 10.2 sp3-sp3 Coupling Reactions Promoted by Silver
Salts. 10.3 sp3-sp2 Coupling Reactions Promoted by Silver Salts. 10.4
sp3-sp Coupling Reactions Promoted by Silver Salts. 10.5 sp2-sp2 Coupling
Reactions Promoted by Silver Salts. 10.6 sp2-sp Coupling Reactions Promoted
by Silver Salts. 10.7 sp-sp Coupling Reactions Promoted by Silver Salts.
10.8 Conclusion. References. 11 Supramolecular Chemistry of Silver (Wei-Yin
Sun, Zheng-Shuai Bai, and Jin-Quan Yu). 11.1 Introduction. 11.2 Cage-Like
Complexes. 11.3 Tube-Like Compounds. 11.4 Polycatenanes with Silver(I).
11.5 Polyrotaxanes with Silver(I). 11.6 Silver(I) Coordination Polymers
with Specific Topology. 11.7 Conclusion. Acknowledgments. References. 12 A
Critical Comparison: Copper, Silver, and Gold (A. Stephen K. Hashmi). 12.1
Introduction. 12.2 Reactions Catalyzed by Copper, Silver, or Gold. 12.3
Reactions Catalyzed by Silver or Gold. 12.4 Reactions Catalyzed by Copper
or Silver. 12.5 Conclusion. References. Index.