Unknown

Dataset Information

0

Visible Light-Promoted Beckmann Rearrangements: Separating Sequential Photochemical and Thermal Phenomena in a Continuous Flow Reactor.


ABSTRACT: The Beckmann rearrangement of oximes to amides typically requires strong acids or highly reactive, hazardous electrophiles and/or elevated temperatures to proceed. A very attractive alternative is the in situ generation of Vilsmeier-Haack reagents, by means of photoredox catalysis, as promoters for the thermal Beckmann rearrangement. Investigation of the reaction parameters for this light-induced method using a one-pot strategy has shown that the reaction is limited by the different temperatures required for each of the two sequential steps. Using a continuous flow reactor, the photochemical and thermal processes have been separated by integrating a flow photoreactor unit at low temperature for the electrophile generation with a second reactor unit, at high temperature, where the rearrangement takes place. This strategy has enabled excellent conversions and yields for a diverse set of oximes, minimizing the formation of side products obtained with the original one-pot method.

SUBMITTER: Chen Y 

PROVIDER: S-EPMC6686973 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC6187735 | biostudies-literature
| S-EPMC9321886 | biostudies-literature
2019-07-03 | GSE123406 | GEO
| S-EPMC4293572 | biostudies-literature
| S-EPMC5679624 | biostudies-literature
| S-EPMC3458766 | biostudies-literature
| S-EPMC6498442 | biostudies-literature
| S-EPMC6935867 | biostudies-literature
| S-EPMC7476038 | biostudies-literature
| S-EPMC8150107 | biostudies-literature