LIGHT-PROMOTED, IRON-CATALYSED FORMAL HYDROGENATION OF ORGANIC COMPOUNDS

Project Information

LIONCAT

Grant agreement ID: 799664

DOI

10.3030/799664

Project closed

EC signature date 5 March 2018

Start date 1 October 2018

End date 6 December 2020

Funded under

• EXCELLENT SCIENCE - Marie Skłodowska-Curie Actions

Total cost

€ 183 454,80

EU contribution

€ 183 454,80

Coordinated by

QUEEN MARY UNIVERSITY OF LONDON
United Kingdom

Periodic Reporting for period 1 - LIONCAT (LIGHT-PROMOTED, IRON-CATALYSED FORMAL HYDROGENATION OF ORGANIC COMPOUNDS)

Reporting period: 2018-10-01 to 2020-09-30

Summary of the context and overall objectives of the project

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.

Work performed from the beginning of the project to the end of the period covered by the report and main results achieved so far

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) and an open access version is available in the online repository ChemRxiv (https://doi.org/10.26434/chemrxiv.12380330.v2).
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.

Progress beyond the state of the art and expected potential impact (including the socio-economic impact and the wider societal implications of the project so far)

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.

untitled.jpg