João Vale: Acylsilanes as reagents for the photochemical construction of C-C bonds

A human figure wearing a doctor's hat, with a black silhouette against a purple background.

In his doctoral dissertation, João Vale explored the potential of acylsilanes in new photochemical reactions. The photorearrangement of acylsilanes generates reactive carbenes which may react with various functional groups. In his work, João Vale synthesised molecules to react with these carbenes and to form novel compounds through carbon-carbon bonding reactions.

Photochemistry is a rapidly growing research field closely related to sustainable and green chemistry. Photochemistry promises to replace toxic and expensive reagents with photons that are cheap and environmentally benign.

Solving sustainability problems requires abandoning the reagents and catalysts derived from fossil fuels. In synthetic chemistry, there is a strong demand to develop processes where visible light is used as an energy source. In addition to these advantages, photochemistry allows completely different reactivity profiles compared to traditional organic chemistry.

Acylsilanes are a class of compounds that stands out due to their ability to efficiently absorb visible light and rearrange to reactive carbenes. These carbenes are highly energetic and can be utilized for various chemical reactions.

“These acylsilane derived carbenes have huge synthetic potential. However, the lack of useful carbon-carbon bond forming reactions limits their usage,” says João Vale.

“In order to bring acylsilanes to the hands of organic chemists, we need to develop novel reactions to attract the interest of the community,” he adds.

During his PhD, João Vale studied the photo reactivity of acylsilanes and discovered two new carbon-carbon bond forming reactions that yield new class of molecules.

“This expansion of the reaction toolbox of acylsilanes will hopefully inspire other researchers to utilize them as sustainable reagents,” says João Vale.

João Vale is currently working as a researcher in the Faculty of Farmacy in Lisbon, Portugal. His research interests are still focused on photochemical reactions and design of new photocatalysts.

Public defence on Wednesday 8 March

The doctoral dissertation of MSc (Bioorganic Chemistry) João Vale in the field of organic chemistry titled Photochemical Reactions of Acylsilanes Towards the Construction of Carbon-Carbon Bonds will be publicly examined at the Faculty of Pharmacy of the University of Lisbon at 12:30 on Wednesday 8 March in 2023, at the Great Hall (Salão Nobre, Avenida Prof. Gama Pinto, 1649-003 Lisbon, Portugal). The Opponent will be Professor Maria de Lurdes dos Santos Cristiano from the University of Algarve. The Custos will be Professor Alexandra Brito from the Faculty of Pharmacy of the University of Lisbon.

The doctoral dissertation is available online.

The public defence can be followed via remote connection.

Organiser

The University of Lisbon