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By Shinji Murai

Within the previous couple of years a wide repetoire of equipment for the activation of unreactive natural functionalities and for his or her use in natural synthesis has been constructed. during this quantity, components starting from the activation of C-H bonds to the chemical transformation of dinitrogen are authoritatively mentioned by way of prime specialists within the box. To turn on capability so that it will cleave differently inert chemical bonds. The cleavage and formation of chemical bonds is prime to natural synthesis; those new activation methodologies make hitherto infeasible reactions tremendous effortless and create new possibilities for cutting edge natural modifications, for either and academia. this is often the 1st ebook that offers an intensive and well timed insurance of either inorganic and natural man made elements of bond activation, therefore giving a huge evaluate of the sphere and permitting either inorganic and natural chemists prepared entry to the methodologies concerned.

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Additional info for Activation of Unreactive Bonds and Organic Synthesis (Topics in Organometallic Chemistry, Volume 3)

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3 is found for diphenylacetylene. Electron-withdrawing groups on the acetylene retard the coupling reaction. There are a couple of alternative mechanisms and these await further studies. Ph N N + Ph Ph RhCl(PPh3)3 1-PrOH/HOAc 25 mL/15 µL reflux, 24 h H N N Ph (22) 90% Ruthenium-catalyzed addition of aromatic C–H bond in aromatic ketones to acetylenes occurs site-selectively (Eq. 23) [37]. When trimethylsilyl substituted acetylenes are employed in the reaction, the desired coupling products are obtained with high regioselectivity in excellent yields.

75 References . . . . . . . . . . . . . . . . . . . 76 Topics in Organometallic Chemistry, Vol. 3 Volume Editor: S. Murai © Springer-Verlag Berlin Heidelberg 1999 48 Fumitoshi Kakiuchi, Shinji Murai 1 Introduction One of the most valuable synthetic methods in organic synthesis is the direct use of otherwise unreactive C–H bonds with the aid of transition metal complexes. Since Kleiman and Dubeck reported in 1963 the possibility of cleavage of C–H bonds in azobenzene by Cp2Ni complex [1], many research groups have reported the cleavage of C–H bonds by using stoichiometric amounts of transition metal complexes [2].

An amide functionality can also serve as the directing group for carbonylation at the α C–H bond (Eq. 30) [44]. 4 Insertion of Carbon Monoxide and Isocyanide into the C–H Bond Several examples of transition metal-catalyzed insertions of carbon monoxide and isocyanide into the C–H bond are known. The carbonylation of a C–H bond to an aldehyde requires photoirradiation conditions. Eisenberg et al. have found iridium-[45, 46] or rhodium-catalyzed [47] photocarbonylation of benzene affording benzaldehyde, albeit with low efficiency [45–47].

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