- Selective synthesis of primary amines by reductive amination of ketones with ammonia over supported Pt catalysts
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Supported platinum catalysts are studied for the reductive amination of ketones under ammonia and hydrogen. For a model reaction with 2-adamantanone, Pt-loaded MoOx/TiO2 (Pt-MoOx/TiO2) shows the highest yield of primary amine. The catalyst is effective for the selective transformation of various aliphatic and aromatic ketones to the corresponding primary amines, which demonstrates the first example of the selective synthesis of primary amines by this reaction. The yield of the amine increases with increase in the negative shift of the C£O stretching band in the infrared spectra of adsorbed acetone on the catalysts, suggesting that Lewis acid sites on the support material play an important role in this catalytic system.
- Nakamura, Yoichi,Kon, Kenichi,Touchy, Abeda Sultana,Shimizu, Ken-Ichi,Ueda, Wataru
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p. 921 - 924
(2015/03/18)
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- Selective reductions. Part 60: Chemoselective reduction of organyl azides with dichloroborane-dimethyl sulfide
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The rate and stoichiometry of the reduction of an organyl azide with BH3·THF was examined under standardized conditions at room temperature. Borane derivatives, such as dialkyl-, alkoxy-, and haloboranes were also examined for the reduction of azides. This study revealed BHCl2·SMe2 to be the most suitable reagent for the reduction of azides. The chemoselectivity of this reagent was also studied by reducing n-hexyl azide in the presence of representative series of functional groups, including esters, halides, nitriles, and nitro groups. BHCl2·SMe2 reduces azides in the presence of all of the above functional groups as well as olefins. Taking advantage of the differences in reactivity of BHCl2·SMe2 and BH3·THF or BH3·SMe2, it is now possible to reduce selectively an azide in the presence of olefins or to hydroborate an olefin in the presence of azides by a judicious choice of the reagent.
- Salunkhe, Ashok M.,Veeraraghavan Ramachandran,Brown, Herbert C.
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p. 10059 - 10064
(2007/10/03)
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- DICHLOROBORANE-DIMETHYL SULFIDE, A HIGHLY SELECTIVE REDUCING AGENT FOR REDUCTION OF ORGANYL AZIDES TO AMINES
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Dichloroborane-dimethylsulfide reduces a variety of organyl azides, such as primary, secondary, tertiary, and aromatic to the corresponding amines in excellent yields.Cycloalkyl and benzylic azides are also readily reduced by this reagent.The reduction of azide with BHCl2*SMe2 is highly selective and many functional groups, such as halogen, ester, nitrile, aliphatic and armatic nitro, survice in this process.
- Salunkhe, Ashok M.,Brown, Herbert C.
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p. 7987 - 7990
(2007/10/02)
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