Seminar on Advanced Organic Chemistry I - MC270P20

• Title: Seminar on Advanced Organic Chemistry I
• Czech title: Vybrané kapitoly z organické chemie I
• Guaranteed by: Department of Organic Chemistry (31-270)
• Faculty: Faculty of Science
• Actual: from 2023
• Semester: summer
• E-Credits: 3
• Examination process: summer s.:
• Hours per week, examination: summer s.:2/0, Ex [HT]
• Capacity: unlimited
• Min. number of students: 4
• 4EU+: no
• Virtual mobility / capacity: no
• State of the course: taught
• Language: English
• Note: enabled for web enrollment
• Guarantor: Ing. Ondřej Baszczyňski, Ph.D.
• Teacher(s): Ing. Ondřej Baszczyňski, Ph.D.; doc. Mgr. Radim Hrdina, Ph.D.; doc. RNDr. Jindřich Jindřich, CSc.; prof. RNDr. Martin Kotora, CSc.; Ing. Aleš Machara, Ph.D.; PharmDr. Eliška Matoušová, Ph.D.; doc. RNDr. Jiří Míšek, Ph.D.; Ing. Rafael Navrátil, Ph.D.; RNDr. David Nečas, Ph.D.; Dr. Lukáš Rýček, M.Sc.; prof. RNDr. Jan Veselý, Ph.D.

Annotation

English

Last update: Ing. Ondřej Baszczyňski, Ph.D. (24.01.2023)

The course deals with advanced parts of organic chemistry. Aim of this course is to inform, update, and encourage students about the newest topics and trends in organic chemistry. Basics, as well as the most recent topics from each field, will be discussed, based on the recent publications in top chemistry journals.

The list of topics for 2022/2023 semester

1) C-H functionalization – (R. Hrdina)
2) Borylations – (D. Nečas)
3) Radical reactions and Photoredox catalysis – (L. Rýček)
4) Synthetic electrochemistry – (R. Navrátil)
5) Trends in catalytic synthetic methods – (M. Kotora)
6) Industrial oxidation-reduction processes in API production – (A. Machara)
7) Organocatalysis – (J. Veselý)
8) Biocatalysis – (E. Matoušová)
9) Biokonjugations – (O. Baszczyňski)
10) Chemical probes for chemical biology – (J. Míšek)
11) High-throughput screening (HTS) – (J. Jindřich)

Czech

Last update: Ing. Ondřej Baszczyňski, Ph.D. (24.01.2023)

Přednáškový kurz je zaměřen na pokročilé partie organické chemie. Cílem kurzu je přiblížení vybraných směrů moderní organické chemie, jejich aplikaci, a přesahu do "běžné" organické syntézy. V jedenácti komprimovaných přednáškách se bude možno seznámit, jak se základy dané disciplíny, tak i s nejnovějšími tzv. "up-to-date" trendy v oboru, publikovanými v prestižních chemických časopisech.

1) C-H functionalization – (R. Hrdina)
2) Borylations – (D. Nečas)
3) Radical reactions and Photoredox catalysis – (L. Rýček)
4) Synthetic electrochemistry – (R. Navrátil)
5) Trends in catalytic synthetic methods – (M. Kotora)
6) Industrial oxidation-reduction processes in API production – (A. Machara)
7) Organocatalysis – (J. Veselý)
8) Biocatalysis – (E. Matoušová)
9) Biokonjugations – (O. Baszczyňski)
10) Chemical probes for chemical biology – (J. Míšek)
11) High-throughput screening (HTS) – (J. Jindřich)

For Ph.D. and ERASMUS students in English.

Literature

Last update: Ing. Ondřej Baszczyňski, Ph.D. (24.01.2023)

Jedná se o přehledné články vycházející zejména v časopisech: Nature, Science, Chemical Reviews, Chemical Society Reviews, Angewandle Chemie International Edition, European Journal of Organic Chemistry. Speciální elektronické materiály nejsou k dispozici.

Recomended literature mostly consist of review articles from top journals such as: Nature, Science, Chemical Reviews, Chemical Society Reviews, Angewandle Chemie International Edition, European Journal of Organic Chemistry. Special electronic materials are not included.

Requirements to the exam

Last update: Ing. Ondřej Baszczyňski, Ph.D. (24.01.2023)

Písemná zkouška v rozsahu přednášené látky a dodaných aktuálních materiálů z časopisecké literatury.

 

Informace o způsobu výuky v případě zavedení distančního studia. Information regarding remore (online)  teaching.

a) Přednášky budou probíhat přes internet (zřejmě přes Google Meet).   Lectures will be presneted online.

b) Adresa konání přednášky bude zaslána přes SIS před zahájením.  The address of a presentation will be sent to you priot to the respective presentation.

c) Ke komunikaci se mají (musí) používat pouze adresy s příponou: @natur.cuni.cz. V případě používaní jiných adres nelze zaručit správnou kvalitu spojení a přístup.

Upozornění: Tyto informace se mohou měnit na základě bezprostředních změn v závislosti na změně vnitřních doporučení a předpisů odrážejících epidemiologickoou situaci. If there will be any changes, you will be informed in due time.

 

Syllabus

English

Last update: Ing. Ondřej Baszczyňski, Ph.D. (24.01.2023)

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.

 

Czech

Last update: Ing. Ondřej Baszczyňski, Ph.D. (24.01.2023)

Sylabus přednáškového kurzu:

Vybrané kapitoly z organické chemie - 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.