SubjectsSubjects(version: 954)
Course, academic year 2019/2020
  
Advanced organic chemistry - AP110014
Title: Advanced organic chemistry
Guaranteed by: Department of Organic Chemistry (110)
Faculty: Faculty of Chemical Technology
Actual: from 2019 to 2021
Semester: both
Points: 0
E-Credits: 0
Examination process:
Hours per week, examination: 3/0, other [HT]
Capacity: winter:unknown / unknown (unknown)
summer:unknown / unknown (unknown)
Min. number of students: unlimited
State of the course: taught
Language: English
Teaching methods: full-time
Teaching methods: full-time
Level:  
Note: can be fulfilled in the future
you can enroll for the course in winter and in summer semester
Guarantor: Tobrman Tomáš doc. Ing. Ph.D.
Jahn Ullrich Dr. habil.
Interchangeability : P110014
Examination dates   Schedule   
Annotation -
Modern principles and mechanisms of organocatalytic, radical, and transition metal-catalyzed reactions will be discussed.
Last update: Tobrman Tomáš (12.05.2022)
Aim of the course -

Students will be able to:

Explain the mechanisms of transition metal-catalyzed reactions.

Explain the mechanisms of radical reactions.

Basic principles of organocatalysis.

Last update: Tobrman Tomáš (12.05.2022)
Literature -

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

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

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

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

R: 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

Last update: Pátková Vlasta (19.11.2018)
Teaching methods -

lectures with practical examples

Last update: Pátková Vlasta (19.11.2018)
Syllabus -

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: Sharpless epoxidation and dihydroxylation, Jacobsen epoxidation, Noyori hydrogenation, transfer hydrogenation, allylic substitution, cyclopropanation, carbonyl addition reactions.

8. Transition metal-catalyzed site-selective functionalization of complex molecules: (C sp3) H activation, metallocarbenes.

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.

Last update: Tobrman Tomáš (12.05.2022)
Entry requirements -

none

Last update: Pátková Vlasta (19.11.2018)
Registration requirements -

none

Last update: Pátková Vlasta (19.11.2018)
Course completion requirements -

Student has to pass the written exam

Last update: Pátková Vlasta (19.11.2018)
 
VŠCHT Praha