Heterocyclization and solvent interception upon oxidative triflamidation of allyl ethers, amines and silanes

• DOI: 10.1016/j.tet.2020.131374
• Publication Date: 2020-07-16T15:49:53Z
• Authors: Anton S. Ganin; Mikhail Yu. Moskalik; Vera V. Astakhova; Irina V. Sterkhova; Bagrat A. Shainyan
• Keywords: Silanes; Interception; Base (topology)

Abstract The reactions of triflamide with a series of mono- and diallyl heteroatomic compounds have been studied in the presence of various oxidants (t-BuOI, NBS, NIS). The reaction course was found to be strongly dependent on the oxidant leading to the products of bis(triflamidation) or heterocyclization in the system (t-BuOCl + NaI), or amidines – the Ritter-type solvent interception halosulfamidation products – with N-bromo- or N-iodosuccinimide. The amidines were converted to imidazolines in high yield via the base-induced heterocyclization.