Download Organometallics as Catalysts in the Fine Chemical Industry by Johannes G. de Vries (auth.), Matthias Beller, Hans-Ulrich PDF

By Johannes G. de Vries (auth.), Matthias Beller, Hans-Ulrich Blaser (eds.)

Johannes G. de Vries: Pd-catalyzed coupling reactions.- Gregory T. Whiteker and Christopher J. Cobley: functions of Rhodium-Catalyzed Hydroformylation within the Pharmaceutical, Agrochemical and body spray Industries.- Philippe Dupau: Ruthenium-catalyzed Selective Hydrogenation for style and body spray Applications.- Hans-Ulrich Blaser, Benoît Pugin and Felix Spindler: uneven Hydrogenation.- Ioannis Houpis: Case research: Sequential Pd-catalyzed Cross-Coupling Reactions; demanding situations on Scale-up.- Adriano F. Indolese: Pilot Plant Scale Synthesis of an Aryl-Indole - Scale up of a Suzuki Coupling.- in step with Ryberg: improvement of a gentle and powerful approach for Palladium Catalysed Cyanation on huge Scale.- Cheng-yi Chen: program of Ring ultimate Metathesis technique to the Synthesis of Vaniprevir (MK-7009), a 20-Membered Macrocyclic HCV Protease Inhibitor.

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A competitive route via a direct Suzuki coupling was also investigated but found less economic. Palladium-Catalysed Coupling Reactions 23 OMe MgBr Br F MeO Pd(OAc)2/PPh3 F 132 F F 133 134 1. HBr/HOAc 2. NiCl2(dppp) DIBALH THF, 15-20 °C OHC 2. G. de Vries Ranbaxy has a patent application on the production of Cinacalcet hydrochloride 23 in which the Kumada–Corriu reaction is used. They use 5 mol% of Fe(acac)3 as catalyst in the reaction between vinyl chloride 136 and Grignard reagent 137, and the coupling product was isolated in 70% yield (Scheme 31) [88].

CHO O Si 12 Highly selective asymmetric hydroformylation of vinyl acetate has been reported on 150-g scale by Landis and Klosin [17]. 8%ee and 139:1 branched/linear. The branched aldehyde was converted to chiral isoxazolines and imidazoles through its hydroximoyl chloride derivative. Reductive amination of aldehydes prepared from hydroformylation is a useful route to amines. Botteghi, et al. reported the synthesis of racemic Tolterodine by sequential hydroformylation-reductive amination [18]. Hydroaminomethylation (tandem hydroformylation/reductive amination) has recently been used to prepare a wide variety of pharmaceutical compounds [19].

The catalyst turnover was 3,000. A competitive route via a direct Suzuki coupling was also investigated but found less economic. Palladium-Catalysed Coupling Reactions 23 OMe MgBr Br F MeO Pd(OAc)2/PPh3 F 132 F F 133 134 1. HBr/HOAc 2. NiCl2(dppp) DIBALH THF, 15-20 °C OHC 2. G. de Vries Ranbaxy has a patent application on the production of Cinacalcet hydrochloride 23 in which the Kumada–Corriu reaction is used. They use 5 mol% of Fe(acac)3 as catalyst in the reaction between vinyl chloride 136 and Grignard reagent 137, and the coupling product was isolated in 70% yield (Scheme 31) [88].

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