Metal-free α-CH amination of ethers with hypervalent sulfonylimino-λ3-bromane that acts as an active nitrenoid.
نویسندگان
چکیده
Hypervalent N-triflylimino-λ(3)-bromane undergoes direct and regioselective α-C-H amination of ethers at room temperature under transition metal-free conditions. Kinetic results, substituent and deuterium isotope effects suggest an asynchronous concerted organonitrenoid transition state with some hydride transfer character, analogous to that for alkane C-H insertions.
منابع مشابه
Organocatalytic nitrenoid transfer: metal-free selective intermolecular C(sp3)–H amination catalyzed by an iminium salt† †Electronic supplementary information (ESI) available: Experimental procedures, characterization data for all new products, copies of NMR spectra. See DOI: 10.1039/c7sc03968a
This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp)–H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87...
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عنوان ژورنال:
- Chemical communications
دوره 48 43 شماره
صفحات -
تاریخ انتشار 2012