SubjectsSubjects(version: 855)
Course, academic year 2019/2020
  
Advanced organic chemistry - AP110014
Title: Advanced organic chemistry
Guaranteed by: Department of Organic Chemistry (110)
Actual: from 2019
Semester: both
Points: 0
E-Credits: 0
Examination process:
Hours per week, examination: 3/0 other [hours/week]
Capacity: winter:unknown / unknown (unknown)
summer:unknown / unknown (unknown)
Min. number of students: unlimited
Language: English
Teaching methods: full-time
Level:  
For type: doctoral
Note: you can enroll for the course in winter and in summer semester
Guarantor: Jahn Ullrich Dr. habil.
Tobrman Tomáš doc. Ing. Ph.D.
Interchangeability : P110014
Annotation -
Last update: Pátková Vlasta (19.11.2018)
Modern principles and mechanisms of organocatalytic, radical, and transition metal catalyzed reactions will be discussed.
Aim of the course -
Last update: Pátková Vlasta (19.11.2018)

Students will be able to:

explain the mechanisms of transition metal catalyzed reactions

explain the mechanisms of radical reactions

basic principles of organocatalysis

Literature -
Last update: Pátková Vlasta (19.11.2018)

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

Teaching methods -
Last update: Pátková Vlasta (19.11.2018)

lectures with practical examples

Syllabus -
Last update: Pátková Vlasta (19.11.2018)

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.

Entry requirements -
Last update: Pátková Vlasta (19.11.2018)

none

Registration requirements -
Last update: Pátková Vlasta (19.11.2018)

none

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

Student has to pass the written exam

 
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