Lectures: 16 h - Tutorials: 4 h

Objectives

The goal of this course is to illustrate how the understanding of the reactivity of organic compounds at the molecular level is essential for the design and elaboration of simple to more complex molecular architectures, which can find applications in various domains (biology, material science...). The course will focus on important chemoselective synthetic tools in organic chemistry, fundamental operations including oxidation and reduction reactions, functional group interconversions, as well as strategies for the formation of carbon-carbon or carbon-heteroatom bonds. The key contribution of heteroelements main group organometallic chemistry and transition metal-catalysis to the field of organic synthesis will be outlined. Selected applications in polymer chemistry, drug discovery, medicinal chemistry and chemical biology will be presented.

Syllabus

1. Introduction
   
2. Oxidation
   
   
   • Alcohols oxidation
     
   • Epoxidation
     
   • Dihydroxylation, oxidative cleavage
     
   • Beckmann rearrangement
     
   • Baeyer-Villiger rearrangement
   
   
3. Functional groups interconversion
   
   
   • Conversion of alcohols into sulfonate esters and halides
     
   • Nucleophilic substitutions
     
   • Mitsunobu reaction
     
   • Acid derivatives interconversion (esterification, amidation)
   
   
4. Reductions
   
   
   • Reductive agents
     
   • Acid derivatives and nitriles reduction
     
   • Aldehydes and ketones reduction
     
   • Reduction of alpha,beta unsaturated aldehydes and ketones
     
   • Stereoselective reduction (Felkin-Anh, Cram-chelate models)
     
   • Reductive amination
     
   • Halides reduction
     
   • Radical deoxygenation and decarboxylation
     
   • Alkenes and alkynes reduction
   
   
5. Main group organometallic chemistry
   
   
   • Synthesis and reactivity of Grignard reagents and organolithium reagents
     
   • Synthesis and reactivity of organozinc reagents
     
   • Synthesis and reactivity of organocuprates
   
   
6. Palladium-catalyzed cross-coupling reactions
   
   
   • Catalytic cycle and elementary steps
     
   • Suzuki-Miyaura cross-coupling
     
   • Sonogashira cross-coupling
     
   • Hartwig-Buchwald cross-coupling
     
     Requirements : A knowledge of the fundamentals of organic chemistry is required. The student should be aware of the basic reactivity profiles of the most important functional groups in organic synthesis (alkenes, alkynes, carbonyl compounds, carboxylic acid derivatives) and be able to write reasonable mechanisms.
     
     Evaluation mechanism : Written exam with course questions and problems
     
     Last Modification : Saturday 8 December 2018