“Novel strategies in organic synthesis”

Prof.sse De Risi e Fantinati

Primo modulo (docente: Dott.ssa Anna Fantinati)
Use of transition metals for the synthesis of fine chemicals
4/03: Aula C1 (Palazzo Manfredini), ore 14:00-16:00
5/03: Aula C1 (Palazzo Manfredini), ore 14:00-16:00
6/03: Aula C1 (Palazzo Manfredini), ore 14:00-16:00

Secondo modulo (docente: Dott.ssa Carmela De Risi)
Multicomponent reactions (MCRs) and domino reactions
10/03: Aula C1 (Palazzo Manfredini), ore 14:00-16:00
11/03: Aula C1 (Palazzo Manfredini), ore 14:00-16:00
12/03: Aula C1 (Palazzo Manfredini), ore 14:00-16:00

Course content:
The course, specifically designed for doctoral students, aims to provide knowledge of innovative organic synthesis. In
particular, the course consists of 12 hours of frontal lessons and is divided into two modules of 6 hours each.
The first module will deal with the use of transition metals for the synthesis of fine chemicals. At first, the general
properties of organometallic complexes will be defined, namely the 18 electron rule, electron counting, oxidation state
and hapto number, then the most common ligands used in transition metal complexes will be described. In terms of
reactivity, the most important cross-coupling reactions promoted by palladium-based catalysts will be analysed,
including Suzuki, Negishi, Sonogashira and Heck reactions, as well as the Buchwald-Hartwig amination, with
particular regard to their use for the synthesis of heterocycles and their application in pharmaceutical chemistry.
Typical examples of secondary cross-coupling reactions will be also considered, as Kumada reaction. Furthermore, C-H
bond activation/functionalisation reactions and cross-metathesis reactions will be described.

The second module will focus on multicomponent reactions (MCRs) and domino reactions. For both types of
transformation, general concepts will first be provided, then some typical reactions will be analysed in detail, paying
particular attention to the mechanistic aspects. With particular regard to multicomponent reactions, the most common
MCRs used in organic synthesis for the preparation of pharmacologically and medicinally relevant scaffolds will be
described, such as Betti, Hantzsch, Biginelli, Passerini and Ugi reactions, with an eye also to their variants, their
stereoselective versions, and possible applications in drug discovery. As for domino reactions, their use in total
synthesis and in organocatalytic processes will be presented. In the first case, representative examples of the main classes of domino reactions will be discussed, that is electrophilic, nucleophilic, radical, pericyclic, and transition metal-
promoted domino reactions; in the second case, the application of typical organocatalytic approaches to domino processes will be illustrated: these will include domino reactions via aminocatalysis, Brønsted acid catalysis, H-bonding
catalysis, and NHC catalysis, together with examples based on combined catalysis.
The knowledge acquired will allow the doctoral student to realise original syntheses featuring high chemical efficiency
in several fields, such as the pharmaceutical, agro-chemical and industrial ones.

obbligatoria la presenza ad almeno 2/3 delle lezioni; possibile attivare il collegamento in streaming solo per
chi si trova all'estero per motivi di studio/ricerca.