Advanced Organic Chemistry - MC270P105

• Title: Advanced Organic Chemistry
• Guaranteed by: Department of Organic Chemistry (31-270)
• Faculty: Faculty of Science
• Actual: from 2023
• Semester: summer
• E-Credits: 0
• Examination process: summer s.:
• Hours per week, examination: summer s.:3/0, Ex [HT]
• Capacity: unlimited
• Min. number of students: unlimited
• 4EU+: no
• Virtual mobility / capacity: no
• State of the course: taught
• Language: English
• Note: course is intended for doctoral students only; enabled for web enrollment
• Guarantor: prof. RNDr. Jan Veselý, Ph.D.
• Teacher(s): Dr. Ullrich Jahn, Ph.D.; prof. Ing. Pavel Kočovský; doc. Ing. Tomáš Tobrman, Ph.D.; prof. RNDr. Jan Veselý, Ph.D.

Annotation

Last update: prof. RNDr. Jan Veselý, Ph.D. (04.06.2021)

This course covers selected areas from organic chemistry, including asymmetric aminocatalysis and H-bonding catalysis, transition metal catalyzed multicomponent and asymmetric reactions, and radical functionalization reactions and radical cascades.

Literature

Last update: PharmDr. Eliška Matoušová, Ph.D. (10.05.2021)

Z: Carey F.A., Sundberg R.J.: Advanced Organic Chemistry,Part A, Springer, New York, DOI:10.1007/978-0-387-44899-2

Z: Carey F.A., Sundberg R.J.: Advanced Organic Chemistry,Part B Springer, New York, DOI:10.1007/978-0-387-71481-3

D: P. I. Dalko: Comprehensive Enantioselective Organocatalysis: Catalysts, Reactions, and Applications, 2013, Wiley‐VCH Verlag GmbH & Co. KGaA, DOI:10.1002/9783527658862

D: Robert H. Crabtree: The Organometallic Chemistry of the Transition Metals, 2014, John Wiley & Sons, Inc., DOI:10.1002/9781118788301

D: H. Togo: Advanced Free Radical Reactions for Organic Synthesis, 2004 Elsevier B.V., https://doi.org/10.1016/B978-0-08-044374-4.X5000-2

Requirements to the exam

Last update: prof. RNDr. Jan Veselý, Ph.D. (04.06.2021)

Requirements for study control:

examination - written exam with score above 60%

Syllabus

Last update: prof. Ing. Pavel Kočovský (15.01.2024)

The subject covers following topics:

1. Catalysis with covalently bound organocatalysts (enamine, iminium, NHC, etc.) - single transformations, domino reactions, application in total synthesis.

2. Catalysis with non-covalently bound organocatalysts (thio-ureas, phosphoric acids, amides, etc.) and multifunctional catalysis - single transformations, domino reactions, application in total synthesis.

3. Introduction to transition metal-catalyzed reactions: mechanisms of transition metal catalyzed reactions, type and properties of ligands, effect of additives on reaction outcomes,

C-C, C-N, C-S, C-N, C-P bond forming reactions.

4. Activation of unreactive C-O, C-C, C-H bonds, transition metal catalyzed halogenations.

5. Transition metal-catalyzed multicomponent reaction - introduction to multicomponent reactions, examples of multicomponent reactions, transition metal-catalyzed multicomponent reactions.

6. Transition metal-catalyzed reactions of allenes.

7. Transition metal-catalyzed asymmetric reactions: Oxy-metalation and amido-metalation of olefins, metal-catalyzed cyclizations, Sharpless epoxidation and dihydroxylation, Jacobsen epoxidation, Noyori hydrogenation, transfer hydrogenation, allylic substitution, cyclopropanation, aziridination, multi-metal catalysis.

8. Site-selective functionalization and molecular editing of complex molecules: C(sp3)-H activation, metallocarbenes, allylic rearrangements, directed remote functionalization, innate functionalization, insertion reactions.

9. Radicals, carbenes and nitrenes: electronic structure, general reactivity patterns, polar effects, reactivity of triplet carbenes and nitrenes.

10. Radical functionalization reactions, radical addition reactions, radical cyclization reactions.

11. Radical cascade reactions and applications in total synthesis.

12. Photochemical radical reactions, emerging technologies of radical chemistry: (photo)redox catalysis, radical catalysis, application of radicals in materials and biology.

Entry requirements

Last update: prof. RNDr. Jan Veselý, Ph.D. (04.06.2021)

The applicants should have a knowledge of basic organic chemistry, at least at the level discussed in John McMurry: Organic Chemistry, 8th ed. Brooks/Cole 2012.

Registration requirements

Last update: prof. RNDr. Jan Veselý, Ph.D. (04.06.2021)

Applicants should have an intermediate knowledge of organic chemistry and be familiar with principles of organic synthesis.