Unit:
Κατεύθυνση Οργανική Σύνθεση και Εφαρμογές της στη Χημική ΒιομηχανίαLibrary of the School of Science
Supervisors info:
Χριστόφορος Κόκοτος, Επίκουρος Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Δημήτριος Γεωργιάδης, Αναπληρωτής Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Γεώργιος Βουγιουκαλάκης, Επίκουρος Καθηγητής, Τμήμα Χημείας, ΕΚΠΑ
Original Title:
Μελέτη Μικρών Οργανικών Μορίων ως Φωτοκαταλυτών για Οργανικούς Μετασχηματισμούς
Translated title:
Small Organic Molecules as Photocatalysts for Organic Transformations
Summary:
Photoorganocatalysis constitutes a rapidly developing field of Organic Synthetic Chemistry, that has raised organic chemists’ interest globally. A new family of organic compounds in the presence of visible light, catalyzes organic transformations successfully, towards the synthesis of pharmaceutical and industrial interest molecules. In the first chapter, Photocatalysis is introduced, along with a classification of the most important organic photocatalysts and their applications in synthesis. The second chapter refers to a literature report on the hydroxylation reaction of aryl boronic acids towards the formation of biologically and industrially important phenols. In the third chapter, the literature background on the hydroacylation reaction of activated alkenes is described. The aim of the present thesis (fourth chapter) was the development of a photoorganocatalytic protocol for the synthesis of phenols from aryl boronic acids and the study on the hydroacylation of Michael acceptors, utilizing different benzaldehydes as photocatalysts. In the fifth chapter, we describe thoroughly the development of an eco-friendly protocol for the synthesis of phenols from aryl boronic acids. With 2,2-dimethoxy-phenylacetophenone as the photoinitiator, air as the oxidant and household bulbs as source of irradiation, our photoorganocatalytic protocol is implemented in a wide range of boronic acids, leading to the corresponding phenols in good yields, under mild reaction conditions. In the sixth chapter, the extensive research upon using benzaldehydes as photocatalysts on the hydroacylation reaction of Michael acceptors is described. para-Cyanobenzaldehyde stands out as the best photocatalyst among 25 benzaldehydes, both in the terms of yield and selectivity. This green methodology is applicable in a variety of substrates and the suggested reaction mechanism is supported by plethora of mechanistic experiments.
Main subject category:
Science
Keywords:
phenols, arylboronic acids, hydroacylation, benzaldehydes, Michael acceptors
