{"product_id":"the-stille-reaction-isbn-9780471312734","title":"The Stille Reaction","description":"A guide to making optimal use of one of the most important tools available to today's synthetic organic chemist\u003cbr\u003e \u003cbr\u003e Compatible with virtually all functional groups without protection and capable of forming carbon-carbon bonds under neutral conditions-often with complete stereospecificity-the Stille reaction is an indispensable component of the synthetic organic chemist's toolkit. In the years since Stille's pioneering work, chemists have developed a vast number of applications for this incredibly versatile metal-catalyzed cross-coupling reaction. This paperback edition of the 50th volume in the definitive Organic Reactions series describes many of those uses.\u003cbr\u003e \u003cbr\u003e Drawing upon their considerable experience as professional synthetic organic chemists who have worked extensively with the Stille reaction, the authors approach their subject from the preparative viewpoint, paying particular attention throughout to limitations, interfering influences, effects of structure, and the selection of experimental techniques. Focusing primarily on the single reaction of the Stille reaction, they provide comprehensive coverage of:\u003cbr\u003e * Experimental conditions and selecting optimal experimental parameters\u003cbr\u003e * Traditional and recently developed experimental procedures\u003cbr\u003e * Side reactions and techniques for avoiding them\u003cbr\u003e * Documented reactions-33 tables list 570 reactions, complete withconditions, yields, structures of major products, and common failures\u003cbr\u003e * Easy-to-follow recipes for casual users of the Stille reaction\u003cbr\u003e \u003cbr\u003e The Stille Reaction is an indispensable working resource for all synthetic organic chemists, especially medicinal chemists. It is also an excellent graduate-level text for students of organic and medicinal chemistry.Die Stille-Reaktion ist eine der sehr wenigen Reaktionen, in denen unter milden Bedingungen Kohlenstoff-Kohlenstoff-Bindungen geknüpft werden können. Man verwendet die Reaktion häufig in der Synthese komplizierter Moleküle zur Verknüpfung größerer Molekülbausteine. Die Autoren diskutieren vom präparativen Standpunkt aus Grenzen, Einflüsse, strukturelle Effekte und die Wahl der geeigneten Reaktionsbedingungen. Mit ausführlichen Vorschriften und vielen Beispielen. (11\/98) MECHANISTIC CONSIDERATIONS, REGIOCHEMISTRY AND STEREOCHEMISTRY.\u003cbr\u003e \u003cbr\u003e SCOPE AND LIMITATIONS: THE ELECTROPHILE.\u003cbr\u003e \u003cbr\u003e Alkenyl Halides.\u003cbr\u003e \u003cbr\u003e Aryl and Heterocyclic Halides.\u003cbr\u003e \u003cbr\u003e Acyl Chlorides.\u003cbr\u003e \u003cbr\u003e Allylic, Benzylic, and Propargylic Electrophiles.\u003cbr\u003e \u003cbr\u003e Alkenyl Sulfonates and Other Electrophiles.\u003cbr\u003e \u003cbr\u003e Aryland Heterocyclic Sulfonates and Other Derivatives.\u003cbr\u003e \u003cbr\u003e Miscellaneous Electrophiles.\u003cbr\u003e \u003cbr\u003e SCOPE AND LIMITATIONS: THE STANNANE.\u003cbr\u003e \u003cbr\u003e Alkylstannanes.\u003cbr\u003e \u003cbr\u003e Alkenylstannes.\u003cbr\u003e \u003cbr\u003e Aryl and Heterocyclic Stannanes.\u003cbr\u003e \u003cbr\u003e Alkynylstannanes.\u003cbr\u003e \u003cbr\u003e Allylstannanes.\u003cbr\u003e \u003cbr\u003e Other Stannanes.\u003cbr\u003e \u003cbr\u003e CARBONYLATIVE COUPLINGS.\u003cbr\u003e \u003cbr\u003e Alkenyl Halides.\u003cbr\u003e \u003cbr\u003e Aryl and Heterocyclic Halides.\u003cbr\u003e \u003cbr\u003e Allylic and Benzylic Halides.\u003cbr\u003e \u003cbr\u003e Alkenyl Sulfonates.\u003cbr\u003e \u003cbr\u003e Aryl and Heterocyclic Sulfonates.\u003cbr\u003e \u003cbr\u003e Miscellaneous Substrates.\u003cbr\u003e \u003cbr\u003e COMPLEX SYNTHETIC SEQUENCES INVOLVING TIN-TO-PALLADIUM (II) METATHESIS STEPS.\u003cbr\u003e \u003cbr\u003e SIDE REACTIONS.\u003cbr\u003e \u003cbr\u003e Homocoupling Reactions.\u003cbr\u003e \u003cbr\u003e Transfer of \"Nontransferable\" Ligands.\u003cbr\u003e \u003cbr\u003e Destannylation.\u003cbr\u003e \u003cbr\u003e Cine Substitution.\u003cbr\u003e \u003cbr\u003e Phosphorus-to-Palladium Aryl Migration.\u003cbr\u003e \u003cbr\u003e Electrophile Reduction.\u003cbr\u003e \u003cbr\u003e Product Isomerization.\u003cbr\u003e \u003cbr\u003e Miscellaneous Side Reactions.\u003cbr\u003e \u003cbr\u003e COMPARISON WITH OTHER METHODS.\u003cbr\u003e \u003cbr\u003e EXPERIMENTAL CONDITIONS.\u003cbr\u003e \u003cbr\u003e The Stannane: Preparation and Handling.\u003cbr\u003e \u003cbr\u003e Alkenyl and Aryl Triflates.\u003cbr\u003e \u003cbr\u003e Choice of Nontransferable Ligands.\u003cbr\u003e \u003cbr\u003e Choice of Catalyst and Ligands.\u003cbr\u003e \u003cbr\u003e Choice of Solvent.\u003cbr\u003e \u003cbr\u003e Additives.\u003cbr\u003e \u003cbr\u003e Workup: Removal of Tin Halides.\u003cbr\u003e \u003cbr\u003e EXPERIMENTAL PROCEDURES.\u003cbr\u003e \u003cbr\u003e Trimethyl([3-(Cyclohexen-1-yl)-2-Propynyl)silane [Cross-Coupling of a Vinyl Halide with an Alkynylstannane Using Pd(PPh_3)_2Cl_2].\u003cbr\u003e \u003cbr\u003e 4-tert Butyl-1-Vinylcyclohexene [Cross-Coupling of a Vinyl Triflate with a Vinylstannane Using Pd(PPh_3)_4 and LiCl].\u003cbr\u003e \u003cbr\u003e 1-(4-Methoxyphenyl)-4-tert-Butylcyclohexene [Cross-Coupling of a Vinyl Triflate with an Arylstannane Using Pd_2(dba)_3 and AsPh_3].\u003cbr\u003e \u003cbr\u003e 3-Methyl-2-(4-Tolyl)-2-Cyclopentenone [Cross-Coupling of an Unreactive Alkenyl Halide under \"Modified\" Conditions Using Pd(PhCN)_2Cl_2 AsPh_3, and Cul as Cocatalyst].\u003cbr\u003e \u003cbr\u003e 1-(4-Nitrophenyl)-2-Propenone (Cross-Coupling of an Acid Chloride with an Arylstannane).\u003cbr\u003e \u003cbr\u003e 4-Allylacetophenone [Cross-Coupling of an Aryl Triflate under Mild Conditions using Tri(2-Furyl)Phosphine as Ligand.\u003cbr\u003e \u003cbr\u003e 8-(Trimethylstannyl)Quinoline (Preparation of an Arylstannane by Cross-Coupling and Aryl Triflate with Hexamethyldistannane).\u003cbr\u003e \u003cbr\u003e 4-(tert-Butyl-1-Vinylcyclohexen-1-Yl)-2-Propenone [Carbonylative Cross-Coupling of an Alkenyl Triflate with an Alkenylstannane using Pd(PPh_3)_4 and LiCl].\u003cbr\u003e \u003cbr\u003e (E)-1-(4-Methoxphenyl)-3-Phenyl-2-Propenone [Carbonylative Cross-Coupling of an Aryl Triflate with an Alkenylstannane using Pd(dppf)Cl_2 and LiCl].\u003cbr\u003e \u003cbr\u003e TUBULAR SURVEY.\u003cbr\u003e \u003cbr\u003e Tables.\u003cbr\u003e \u003cbr\u003e References. VITTORIO FARINA, PhD, is Director at the Boehringer Ingelheim Pharmaceuticals Department of Chemical Development.\u003cbr\u003e \u003cbr\u003e VENKAT KRISHNAMURTHY, PhD, is a research chemist with Occidental Chemical Corporation.\u003cbr\u003e \u003cbr\u003e WILLIAM J. SCOTT is a research chemist with the Bayer Corporation Institute of Chemistry, Department of Medicinal Chemistry. A guide to making optimal use of one of the most important tools available to today's synthetic organic chemist\u003cbr\u003e \u003cbr\u003e Compatible with virtually all functional groups without protection and capable of forming carbon-carbon bonds under neutral conditions-often with complete stereospecificity-the Stille reaction is an indispensable component of the synthetic organic chemist's toolkit. In the years since Stille's pioneering work, chemists have developed a vast number of applications for this incredibly versatile metal-catalyzed cross-coupling reaction. This paperback edition of the 50th volume in the definitive Organic Reactions series describes many of those uses.\u003cbr\u003e \u003cbr\u003e Drawing upon their considerable experience as professional synthetic organic chemists who have worked extensively with the Stille reaction, the authors approach their subject from the preparative viewpoint, paying particular attention throughout to limitations, interfering influences, effects of structure, and the selection of experimental techniques. Focusing primarily on the single reaction of the Stille reaction, they provide comprehensive coverage of:\u003cbr\u003e * Experimental conditions and selecting optimal experimental parameters\u003cbr\u003e * Traditional and recently developed experimental procedures\u003cbr\u003e * Side reactions and techniques for avoiding them\u003cbr\u003e * Documented reactions-33 tables list 570 reactions, complete withconditions, yields, structures of major products, and common failures\u003cbr\u003e * Easy-to-follow recipes for casual users of the Stille reaction\u003cbr\u003e \u003cbr\u003e The Stille Reaction is an indispensable working resource for all synthetic organic chemists, especially medicinal chemists. It is also an excellent graduate-level text for students of organic and medicinal chemistry.","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47990347006181,"sku":"NP9780471312734","price":197.95,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9780471312734.jpg?v=1761787452","url":"https:\/\/k12savings.com\/products\/the-stille-reaction-isbn-9780471312734","provider":"K12savings","version":"1.0","type":"link"}