Periodic Reporting for period 1 - LIONCAT (LIGHT-PROMOTED, IRON-CATALYSED FORMAL HYDROGENATION OF ORGANIC COMPOUNDS)
Reporting period: 2018-10-01 to 2020-09-30
The hydrogenation of C-C multiple bonds and related reductive transformations are among the most important processes in the chemical industry. However, most of the hydrogenation processes are based either on noble metal catalysts containing Pd and Pt or on less expensive but difficult to handle and pyrophoric and require the use of compressed gas. Considering this, the photocatalytic reduction would open a path for the development of greener and safer hydrogenation methodologies, avoiding the use of high-energy, strong reductants as well as the use of pressure equipment.
We have developed wide-scope, efficient protocols using Ir-based photocatalysts for the reduction, and our investigation on this reaction revealed an unusual mechanism involving hydrogen atom transfer. This investigation has been published in Advanced Synthesis and Catalysis (https://doi.org/10.1002/adsc.202000751(opens in new window)) and an open access version is available in the online repository ChemRxiv (https://doi.org/10.26434/chemrxiv.12380330.v2(opens in new window)).
Following this investigation, we discovered an aminoalkylation of alkenes which proceeded with unexpected regioselectivity to afford β-amino esters. Importantly, we developed a continuous-flow application of our method which allowed the efficient and easy preparation of multi-gram amounts of products. A publication including all these results is currently in preparation.
Following this investigation, we discovered an aminoalkylation of alkenes which proceeded with unexpected regioselectivity to afford β-amino esters. Importantly, we developed a continuous-flow application of our method which allowed the efficient and easy preparation of multi-gram amounts of products. A publication including all these results is currently in preparation.
Thus, new methods for transfer hydrogenation and hydrofunctionalisation of olefins have been successfully developed, thus contributing to the development of new chemical technologies for performing sustainable and efficient transformations of alkenes.