One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles
| Authors | |
|---|---|
| Year of publication | 2020 |
| Type | Article in Periodical |
| Magazine / Source | RSC Advances |
| MU Faculty or unit | |
| Citation | |
| Web | Odkaz na plný text výsledku nebo domovskou stránku výsledku. |
| Doi | http://dx.doi.org/10.1039/d0ra04359a |
| Keywords | amides; cyanides; molecular oxygen |
| Description | We have identified a novel one-pot method for the synthesis of beta-amino alcohols, which is based on C-H bond hydroxylation at the benzylic alpha-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. |
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