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Intermolecular Allene Functionalization by Silver-Nitrene Catalysis

Journal of the American Chemical Society | 28 Jun 2020

MR Rodríguez, M Besora, F Molina, F Maseras, MM Diaz-Requejo and PJ Pérez
Abstract
Under silver catalysis conditions, using [Tp*,BrAg]2 as the catalyst precursor, allenes react with PhI=NTs in the first example of efficient metal-mediated intermolecular nitrene transfer to such substrates. The nature of the substituent at the allene seems crucial for the reaction outcome since arylallenes are converted into azetidine derivatives whereas methylene aziridines are the products resulting from alkylallenes. Mechanistic studies allow proposing that azetidines are formed through unstable cyclopropylimine intermediates which further incorporates a second nitrene group, both processes being silver-mediated. Methylene aziridines from alkylallenes derive from catalytic nitrene addition to the allene double bonds. Both routes have result-ed productive for further synthetic transformations affording aminocyclopropanes.
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