Syllabus:

Seminar on Advanced Organic Chemistry - 2022/23

1) C-H functionalization – (Radim Hrdina)

In this lecture we will discuss methods to cleave a C-H bond in aliphatic and aromatic organic compounds. Keywords are directed and undirected functionalizations with different electrophiles promoting insertion reactions, C-H activation reactions, hydrogen atom transfer reactions, hydride shift reactions and electrophilic aromatic substitution reactions.

2) Borylations – (David Nečas)

Catalytic borylation of organic compounds, effect of catalyst on regioselectivity, directing groups, conversion of boronic acid derivatives into mother functional groups.

3) Radical reactions and Photoredox catalysis – (Lukáš Rýček)

Persistent radical effect (PRE), redox-active esters, principle of photocatalysis in radical reactions, hydrogen atom transfer (HAT) in nature and laboratory. Plus, some recent news and trends in photoredox catalysis.

4) Synthetic electrochemistry – (Rafael Navrátil)

News and trends in synthetic electrochemistry.

5) Trends in catalytic synthetic methods – (Martin Kotora)

The lecture will deal with selected topics of modern synthetic methods and their application in functionalization and modification of natural and bioactive compounds. The topics will encompass transition metal catalyzed reductive radical reactions, C-H activations, and Wacker oxidation.

6) Industrial oxidative and reductive processes in API production – (Aleš Machara)

The lecture covers the issue of API production in the pharmaceutical industry, taking into account enantioselective reduction as a key method of introducing chiral center. In the introduction, reduction catalysts are presented according to the type of transition metal and the type of solid support. Also, chiral ligands for enantioselective reactions are discussed. In short, some oxidative reactions used for the production of specific APIs are also presented. Last but not least, the issue of transition metal residues in the API, FDA limits and methods used to reduce contamination are discussed.

7) Organocatalysis – (Jan Veselý)

Covalent organocatalysis, including aminocatalysis, NHC catalysis, and non-covalent organocatalysis, such as H-bonding and Bronsted acid catalysis. Cooperative and bifunctional catalysis.

8) Biocatalysis – (Eliška Matoušová)

Features of biocatalysis, biocatalytic reactions and their use in organic synthesis.

9) Biokonjugations – (Ondřej Baszczyňski)

Lecture will cover the development of click-chemistry and its application towards bio-conjugations. Then, we examine covalent modification of proteins. Reactivity, chemo-selectivity, scope of particular reactions, and practical aspects will also be discussed.

10) Chemical probes for chemical biology – (Jiří Míšek)

The lecture will address the development and applications of various chemical approaches in chemical biology, including activity-based protein profiling, fluorescent probes, arrays, DNA-encoded libraries, etc. also, the impact of the field on developments in modern biomedical research will be discussed.

11) High-throughput screening (HTS) – (Jindřich Jindřich)

The lecture gives an overview of HTS and the possibilities to perform organic reactions in the HTS mode. In addition, it will describe devices and tools available at the Openscreen.cz facility.