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La combinaison du précatalyseur stable à l'air [CpRu([eta]6-C10H8)] [PF6] avec des ligands de type pyridine-monooxazoline a permis de développer une nouvelle stratégie pour effectuer des réactions de substitution allyliques avec des conditions expérimentales simples. Cette famille de ligands est apparue particulièrement appropriée pour effectuer l'étude de réactions du type réarrangement de Carroll. Le mécanisme de cette réaction a été étudié et un cycle catalytique raisonnable en a découlé. Une stratégie de double activation par co-catalyse a donc été développée: l'utilisation synergique de sels de magnésium a permis d'effectuer ces réactions à température ambiante et donc de manière plus sélective.
Enantioselective C-C Bond Forming Reactions: From Metal Complex-, Organo-, and Bio-catalyzed Perspectives, Volume 73 in the Advances in Catalysis series, highlights new advances in the field, with this new volume presenting interesting chapters on topics such as An introduction to Chirality, Metal-catalyzed stereoselective C-C-bond forming reactions, Enantioselective C-C bond forming reactions promoted by organocatalysts based on unnatural amino acid derivatives, Enantioselective C-C bond formation in complex multicatalytic system, Gold-based multicatalytic systems for enantioselective C-C Bond forming reactions, Novel enzymatic tools for C-C bond formation through the development of new-to-nature biocatalysis, and more. Provides the authority and expertise of leading contributors from an international board of authors Presents the latest release in Advances in Catalysis serials Updated release includes the latest information in the field
This thesis presents the latest developments in new catalytic C–C bond formation methods using easily accessible carboxylate salts through catalytic decarboxylation with good atom economy, and employing the sustainable element iron as the catalyst to directly activate C–H bonds with high step efficiency. In this regard, it explores a mechanistic understanding of the newly discovered decarboxylative couplings and the catalytic reactivity of the iron catalyst with the help of density functional theory calculation. The thesis is divided into two parts, the first of which focuses on the development of a series of previously unexplored, inexpensive carboxylate salts as useful building blocks for the formation of various C–C bonds to access valuable chemicals. In turn, the second part is devoted to several new C–C bond formation methodologies using the most ubiquitous transition metal, iron, as a catalyst, and using the ubiquitous C–H bond as the coupling partner.
Organocatalyzed Reactions I and II presents a timely summary of organocatalysed reactions including: a) Enantioselective C-C bond formation processes e.g. Michael-addition, Mannich-reaction, Hydrocyanation (Strecker-reaction), aldol reaction, allylation, cycloadditions, aza-Diels-Alder reactions, benzoin condensation, Stetter reaction, conjugative Umpolung, asymmetric Friedel-Crafts reactions; b) Asymmetric enantioselective reduction processes e.g. Reductive amination of aldehydes or ketones, asymmetric transfer hydrogenation; c) Asymmetric enantioselective oxidation processes; d) Asymmetric epoxidation, Bayer-Villiger oxidation; e) Enantioselective a-functionalization; f) A-alkylation of ketones, a-halogenation and a-oxidation of carbonyl compounds.
Organocatalyzed Reactions I and II presents a timely summary of organocatalysed reactions including: a) Enantioselective C-C bond formation processes e.g. Michael-addition, Mannich-reaction, Hydrocyanation (Strecker-reaction), aldol reaction, allylation, cycloadditions, aza-Diels-Alder reactions, benzoin condensation, Stetter reaction, conjugative Umpolung, asymmetric Friedel-Crafts reactions; b) Asymmetric enantioselective reduction processes e.g. Reductive amination of aldehydes or ketones, asymmetric transfer hydrogenation; c) Asymmetric enantioselective oxidation processes; d) Asymmetric epoxidation, Bayer-Villiger oxidation; e) Enantioselective a-functionalization; f) A-alkylation of ketones, a-halogenation and a-oxidation of carbonyl compounds.
With contributions by numerous experts
Carbon-carbon bond forming reactions are arguably the most important processes in chemistry, as they represent key steps in the building of complex molecules from simple precursors. Among these reactions, metal-catalyzed cross-coupling reactions are extensively employed in a wide range of areas of preparative organic chemistry, ranging from the synthesis of complex natural products, to supramolecular chemistry, and materials science. In this work, a dozen internationally renowned experts and leaders in the field bring the reader up to date by documenting and critically analyzing current developments and uses of metal-catalyzed cross-coupling reactions. A particularly attractive and useful feature, that enhances the practical value of this monograph, is the inclusion of key synthetic protocols, in experimental format, chosen for broad utility and application. This practice-oriented book can offer the practitioner short cuts to ensure they remain up-to-date with the latest developments.
In 1972, a very powerful catalytic cycle for carbon-carbon bond formation was 2 first discovered by the coupling reaction of Grignard reagents at the sp -carbon. Over the past 30 years, the protocol has been substantially improved and expanded to other coupling reactions of Li,B,N,O,Al,Si,P,S,Cu,Mn,Zn,In,Sn, and Hg compounds. These reactions provided an indispensable and simple methodology for preparative organic chemists. Due to the simplicity and rel- bility in the carbon-carbon, carbon-heteroatom, and carbon-metalloid bo- formations,as well as high efficiency of the catalytic process,the reactions have been widely employed by organic chemists in various fields. Application of the protocol ranges from various syntheses of complex natural products to the preparation of biologically relevant molecules including drugs, and of sup- molecules, and to functional materials. The reactions on solid surfaces allow robot synthesis and combinatorial synthesis. Now, many organic chemists do not hesitate to use transition metal complexes for the transformation of org- ic molecules. Indeed, innumerable organic syntheses have been realized by the catalyzed reactions of transition metal complexes that are not achievable by t- ditional synthetic methods. Among these, the metal-catalyzed cross-coupling reactions have undoubtedly contributed greatly to the development of such a new area of “metal-catalyzed organic syntheses”. An excellent monograph for the cross-coupling reactions and other met- catalyzed C-C bond-forming reactions recently appeared in Metal-catalyzed Cross-coupling Reactions (Wiley-VCH,1998).