An introduction to synthesis using organocopper reagents
Eiichi Nakamura received his Ph.D. from Tokyo Institute of Technology. He first took an academic position at this Institute and in 1995 moved to the University of Tokyo. He has been honored with the Chemical Society of Japan Award (2003), the Humboldt Research Award (2006), the Medal with Purple Ribbon from the Japanese Government (2009), and Arthur C. Cope Scholar Award of the American Chemical Society (2010). He is an Elected Fellow of the American Association for the Advancement of Science (1998), a Fellow of the Royal Society of Chemistry (2005), an Honorary Foreign Member of the American Academy of Arts and Sciences (2008), and an Honorary Member of the Israel Chemical Society (2009). His interests cover the fields of physical organic, synthetic, organometallic, bioorganic, computational/theoretical chemistry, and electron microscopy, all of which focus on reactive intermediates.
14.11 Alkane Synthesis Using Organocopper Reagents
Tables of 1H and 13C NMR chemical shifts have been compiled for common organic compounds often used as reagents or found as products or contaminants in deuterated organic solvents. Building upon the work of Gottlieb, Kotlyar, and Nudelman in the signals for common impurities are now reported in additional NMR solvents (tetrahydrofuran-8, toluene-8, dichloromethane-2, chlorobenzene-5, and 2,2,2-trifluoroethanol-3) which are frequently used in organometallic laboratories. Chemical shifts for other organics which are often used as reagents or internal standards or are found as products in organometallic chemistry are also reported for all the listed solvents.
Cartesian coordinates of representative optimized structures in the organocuprate reaction mechanisms, and a movie of the reductive elimination process in the conjugate addition reaction (cf. Figure ). This material is available free of charge via the Internet at .
They are reagents in organic chemistry
is a comprehensive online resource for synthetic organic chemists. Instead of offering coverage of millions of reactions, it uniquely focuses on 200,000+ of the most important and useful synthetic reactions. These reactions are reviewed and refined by trained chemists (rather than machine selected), resulting in a high quality, verified critical discussion of the use, selection, usability and repeatability of a given reaction.
Vinyl Epoxides in Organic Synthesis.
The alkylcopper species generally have lower stability and reactivity than the cuprates, and are sometimes insoluble, so they are not used extensively. Their solubility and reactivity can be improved by complexation with Lewis acids (BF3 or MgBr2) or Lewis bases (phosphines). The dialkyl cuprates are the most generally useful, and most synthetic applications make use of these. Because only one of the ligands are transferred (after the first transfer the product is a usually unreactive alkylcopper), a variety of mixed cuprates have been developed in which one of the ligands does not transfer rapidly (typically cyanide or an acetylide is used, but many other groups such as other stabilized organolithium reagents (thienyllithium, lithiosulfones), dialkyl amides, phosphides or thiolates can be used.
reactions in organocopper chemistry, Wipf, P
Tables of 1H and 13C NMR resonances for common organic contaminants are reported in 12 different deuterated organic solvents frequently used to study organometallic systems. This manuscript catalogs the chemical shifts for nearly 60 gases and organic compounds which are commonly used as reagents or internal standards or are found as products in organometallic reactions.
Organocopper Reagents - Reference Module in …
F., III, Towards organo-click chemistry: Development of organocatalytic multicomponent reactions through combinations of Aldol, Wittig, Knoevenagel, Michael, Diels-Alder and Huisgen cycloaddition reactions.