Silver in Organic Synthesis

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 C sp 3 -Ag. 1.3 C sp 2 -Ag. 1.4 C sp -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, Aurelien 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 pi 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 sp 3 - sp 3 Coupling Reactions Promoted by Silver Salts. 10.3 sp 3 - sp 2 Coupling Reactions Promoted by Silver Salts. 10.4 sp 3 - sp Coupling Reactions Promoted by Silver Salts. 10.5 sp 2 - sp 2 Coupling Reactions Promoted by Silver Salts. 10.6 sp 2 - 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.