Uncovering the Importance of Proton Donors in TmI2-Promoted Electron Transfer: Facile C−N Bond Cleavage in Unactivated Amides**
نویسندگان
چکیده
منابع مشابه
A Facile and Environmental Friendly Method for C=N Bond Cleavage of Imines Using p-Toluenesulfonic Acid in Solid State
A simple, efficient and clean procedure has been developed for the cleavage of imines C=N bond. Deprotection of imines to their parent carbonyl and amine compounds was achieved using p-toluenesulfonic acid in the solid state condition at 25-45 ˚C. The salient features of this methodology are shorter reaction times, cheap processing, high yields of product and easy availability of the catalyst. ...
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Highly chemoselective direct reduction of primary, secondary, and tertiary amides to alcohols using SmI2/amine/H2O is reported. The reaction proceeds with C-N bond cleavage in the carbinolamine intermediate, shows excellent functional group tolerance, and delivers the alcohol products in very high yields. The expected C-O cleavage products are not formed under the reaction conditions. The obser...
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The internal strain in cyclic amides are explained as a factor of resonance that are effected on the bond length C-N and are a major factor of rates of hydrolysis. The cyclic amides in this study are optimized by Gaussian program and the bond length of C-N in the rings are studied by HF/6-31G*.
متن کاملPhotoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature.
The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as w...
متن کاملInternal strain on the bond length and rate of hydrolysis in cyclic amides
The internal strain in cyclic amides are explained as a factor of resonance that are effected on the bond length C-N and are a major factor of rates of hydrolysis. The cyclic amides in this study are optimized by Gaussian program and the bond length of C-N in the rings are studied by HF/6-31G*.
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عنوان ژورنال:
دوره 52 شماره
صفحات -
تاریخ انتشار 2013