Abstract
The reaction of N-tert-alkyl-substituted propargylic amines with trialkylalanes in the presence of 20 mol.% Cp2ZrCl2 was studied. The pattern of the products depended on the nature of substituents at the nitrogen atom. N-tert-Alkyl-N-arylmethyl-substituted propargylic amines when reacted in CH2Cl2 aff ord a mixture of N-tert-alkyl-N-(arylmethyl)alkylamines and N-tertalkyl-N-(arylmethyl)amines at ratios from {2: 3 to {3: 2 in total yield of 70–95%. In hexane, N-tert-alkyl-N-(arylmethyl)amines are produced selectively. N-Alkyl-N-tert-alkyl-substituted propargylic amines similar to N-isoalkyl-substituted ones underwent a Zr-promoted hydride transfer to aff ord (2E)-alkenylamines in good yield (58–69%).
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Based on the materials of the Russian National Conference “Interplay between Ionic and Covalent Interactions in Design of Molecular and Nano Chemical Systems” (ChemSci-2019) (May 13–17, 2019, Moscow, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0061–0067, January, 2020.
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Ramazanov, I.R., Kadikova, R.N., Saitova, Z.R. et al. Pathways of the reaction between N,N-disubstituted propargylic amines and cationic zirconium complexes. Russ Chem Bull 69, 61–67 (2020). https://doi.org/10.1007/s11172-020-2723-9
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DOI: https://doi.org/10.1007/s11172-020-2723-9