Silver in Organic Chemistry (eBook, PDF)
Redaktion: Harmata, Michael
Silver in Organic Chemistry (eBook, PDF)
Redaktion: Harmata, Michael
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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…mehr
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- Produktdetails
- Verlag: John Wiley & Sons
- Seitenzahl: 422
- Erscheinungstermin: 3. August 2010
- Englisch
- ISBN-13: 9780470597514
- Artikelnr.: 37297605
- Verlag: John Wiley & Sons
- Seitenzahl: 422
- Erscheinungstermin: 3. August 2010
- Englisch
- ISBN-13: 9780470597514
- Artikelnr.: 37297605
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.
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, Aurélien 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 π 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, Aurélien 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.
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, Aurélien 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 π 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, Aurélien 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.