The role of fluorine atoms in drug discovery has become of fundamental importance, due to their ability to confer unprecedented therapeutic profiles on a molecule. In this framework, the trifluoromethylthio group (SCF3) is attracting an increasing attention in pharmaceutical, agrochemical and material chemistry and it is commonly used to modulate lipophilicity, bioavailability and metabolic stability of newly designed molecules. Actually, several drugs whose biological activity is strictly related to the presence of a SCF3 residue in the molecular scaffold are already on the market. Despite trifluoromethylthiolated carbonyl derivatives present a high potential of application in medicinal chemistry, synthetic approaches to alpha-SCF3-substituted carbonyl compounds are still limited, and catalytic strategies to access optically active functionalized carbonyl compounds are almost unexplored. The present review will discuss the use of radical, nucleophilic and electrophilic trifluoromethylthiolating reagents, to synthesize decorated trifluoromethylthio carbonyl derivatives, with a particular attention on catalytic methodologies and stereoselective methods affording enantiomerically enriched molecules.

Synthesis of Alpha-trifluoromethylthio Carbonyl Compounds : A Survey of the Methods for the Direct Introduction of the SCF3 Group on to Organic Molecules / S. Rossi, A. Puglisi, L.M. Raimondi, M. Benaglia. - In: CHEMCATCHEM. - ISSN 1867-3880. - 10:13(2018 Jul 09), pp. 2717-2733. [10.1002/cctc.201800170]

Synthesis of Alpha-trifluoromethylthio Carbonyl Compounds : A Survey of the Methods for the Direct Introduction of the SCF3 Group on to Organic Molecules

S. Rossi
Primo
;
A. Puglisi
Secondo
;
L.M. Raimondi
Penultimo
;
M. Benaglia
Ultimo
2018

Abstract

The role of fluorine atoms in drug discovery has become of fundamental importance, due to their ability to confer unprecedented therapeutic profiles on a molecule. In this framework, the trifluoromethylthio group (SCF3) is attracting an increasing attention in pharmaceutical, agrochemical and material chemistry and it is commonly used to modulate lipophilicity, bioavailability and metabolic stability of newly designed molecules. Actually, several drugs whose biological activity is strictly related to the presence of a SCF3 residue in the molecular scaffold are already on the market. Despite trifluoromethylthiolated carbonyl derivatives present a high potential of application in medicinal chemistry, synthetic approaches to alpha-SCF3-substituted carbonyl compounds are still limited, and catalytic strategies to access optically active functionalized carbonyl compounds are almost unexplored. The present review will discuss the use of radical, nucleophilic and electrophilic trifluoromethylthiolating reagents, to synthesize decorated trifluoromethylthio carbonyl derivatives, with a particular attention on catalytic methodologies and stereoselective methods affording enantiomerically enriched molecules.
carbonyl compounds; electrophilic reagents; fluorinated products; metal catalysts; organocatalysis; trifluoromethylthiolation
Settore CHIM/06 - Chimica Organica
PIANO DI SOSTEGNO ALLA RICERCA 2015-2017 - LINEA 2 "DOTAZIONE ANNUALE PER ATTIVITA' ISTITUZIONALE"
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/582603
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