On May 1 st 2023, Dr. Marco Galeotti started his MSCA postdoctoral project entitled Implementing Cationic Paths in Aliphatic C-H Oxidation (ICAT-PACHO), under the supervision of Prof. Miquel Costas at the Institute of Computational Chemistry and Catalysis (IQCC) of University of Girona (UdG). This 2-year fellowship will allow Dr. Marco Galeotti to start a new project devoted to the study of C(sp 3 )-H bond oxidations with H2O2 catalyzed by biologically inspired iron and manganese catalysts. Additionally, as part of his research, the fellow will carry out a secondment (3 months, Jan 2024 – April 2024) at the Max-Planck-Institut für Kohlenforschung (MPI) in Mülheim an der Ruhr (Germany) under the guidance of Prof. Benjamin List.
Overview of the ICAT-PACHO project:
Going beyond well documented methodologies, the ICAT-PACHO project will investigate a novel cationic path enabling so far unexplored C-H bond elaborations. The challenging goal of the sustainability will be achieved by using earth abundant based catalysts and an environmentally friendly oxidant such as hydrogen peroxide to provide valuable products, with benefits in terms of decreased waste generation and reaction step economy. This project will represent an opportunity to develop an efficient catalytic methodology able to accomplish aliphatic C-H bond oxidations via cationic paths.
About the project:
C(sp 3 )-H bond oxidation is an important class of C-H functionalization reactions because of the ubiquity of oxidized aliphatic frameworks in molecules of biological and pharmaceutical interest, and of the rich chemistry associated to C-O bond elaboration, amenable for broad product diversification. In this context, the development of homogeneous catalysts based on first-row transition metals, that in the presence of hydrogen peroxide mimic the mode of action of oxygenases has represented a breakthrough. C-H bond hydroxylation executed by enzymes and bioinspired catalysts proceeds through a well-established radical mechanism. Side products derived from cationic intermediates are seldom observed. However, cationic paths are particularly interesting because they diverge the chemoselectivity of the C-H oxidation reaction towards valuable products inaccessible via the canonical radical paths. Catalytic C-H oxidation reactions where product chemoselectivity can be reliably manipulated towards cationic paths remains a standing challenge, which realization will provide access to unique structures by manipulation of ubiquitous C(sp 3 )-H bonds. Within this framework, the fellow will develop novel catalytic methodologies to implement cationic paths in C(sp 3 )-H bond oxidation procedures, which are typically dominated by radical mechanisms.
Dr. Marco Galeotti is currently a MSCA Fellow (May.-2023 to April.-2025) in the Bioinspired, Supramolecular and Catalysis Chemistry (QBIS-CAT) research group at the IQCC of UdG. After obtaining the bachelor degree in Chemistry at the University of Rome “Tor Vergata” (2013-2016, full marks with merit: 110/110 cum laude), he coursed the master degree in Chemistry at the University of Rome “Tor Vergata” (2016-2018), being awarded with full marks with merit (110/110 cum laude). After that, he started his PhD in Chemical Sciences (2018-2022, PhD scholarship) at the University of Rome “Tor Vergata” under the supervision of Prof. Massimo Bietti and Prof. Michela Salamone. The research activity has been mostly devoted toward the study of electronic, torsional, hyperconjugative and medium effects in HAT-based C(sp3)-H bond functionalizations promoted by alkoxyl radicals and dioxiranes. These studies have led to a deeper understanding of the factors governing reactivity and selectivity on HAT-based aliphatic C-H bond functionalization, contributing to define useful guidelines to be then employed to implement site- and stereo-selectivity in these transformations. During his PhD, the fellow has benefited of international collaborations with groups specialized in computational (G. A. DiLabio, University of British Columbia and K. N. Houk, University of California Los Angeles) and proton-coupled electron transfer chemistry (J. M. Mayer, Yale University). During a 6-month research stay abroad in the group of Prof. Miquel Costas, he also performed C-H bond oxidations catalyzed by metal-oxo complexes. In 2022, he obtained the PhD title cum laude. Upon graduation, Marco started his postdoc in the group of Prof. Miquel Costas at UdG (2022-present). In February 2023, Marco was awarded a MSCA postdoctoral fellowship to support his research project: “Implementing Cationic Paths in Aliphatic C-H Oxidation”.
Girona, October 17, 2023
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