Silyl hydride in neighboring group-assisted reduction of substituted phenols
“Transformation of compounds into chemicals useful for industrial applications is of great importance with the choice of reagents and catalysts contributing significantly to accessing targeted molecules under environmentally benign conditions”, Benedicta Assoah mentions.
Reductions are among the most versatile and prevailing transformations in synthetic chemistry as most desired molecules are mainly accessible through functional group manipulations of synthetic precursors. Use of silyl hydrides allows efficient reduction of functional groups present in a molecule under mild reaction conditions when facilitated by catalysts. Such reductions are more desirable with non-metal catalysts as they allow for the preparation of value-added products devoid of metal contaminants.
The thesis focuses on the design and preparation of a silyl hydride capable of effecting the reduction of phenolic compounds into targeted molecules in Lewis base–catalyzed reactions. Assoah demonstrates in her thesis an activation mode where the presence of a phenol reinforces the selectivity for the reduction of proximal carbon heteroatom double bonds using a novel chlorohydrosilane expedited by Lewis base catalysts.
“It is envisioned that the designed silyl hydride becomes an effective reagent in the reduction toolbox for various functional groups interconversion. Most importantly, the findings from this research reveals mild and selective synthetic procedures to access substituted phenolic compounds with potential industrial applications”, Assoah notes.
The doctoral dissertation of MSc Benedicta Akuamesu Assoah in the field of Organic Chemistry titled Lewis Base-Catalyzed Modification of Ortho-Substituted Phenols will be publicly examined in the Faculty of Engineering and Natural Sciences at Tampere University in Festia building auditorium FA032, Korkeakoulunkatu 8, Tampere, on 15.11.2019, at noon. The Opponent will be Professor Manolis Stratakis, University of Crete. The Custos will be Adjunct Professor Nuno Rafael Candeias from the Faculty of Engineering and Natural Sciences.
The dissertation is available online at http://urn.fi/URN:ISBN:978-952-03-1321-0
Photo: Eugene Frimpong