Construction of homoallylic trifluoromethylated compounds via fluoride-triggered cross-electrophile coupling

Abstract

Organofluorine compounds are of great importance in modern organic chemistry. These compounds have significant and diverse applications, ranging from the formulation of pharmaceuticals and pesticides to the creation of new materials with valuable properties. Therefore, it is important to emphasize the need to find sustainable and environmentally friendly synthetic routes for their products. In this TFG Project, a venerable reaction in chemistry such as the Asymmetric Allylic Alkylations (AAA) will be applied with more recent concepts like organocatalysis for the sustainable synthesis of complex organofluorine compounds, using fluorinated Morita-Baylis-Hillman adducts (MBHF), gem-difluoroalkenes and fluoride ions. Sustainability should be emphasized because the synthetic reaction developed in this work has a unique feature: the leaving group of the molecule is incorporated into the product, so conceptually the reaction is 100% atom economical. The developed protocol forms trifluoromethylated homoallylic products in regioselective and diastereoselective (E/Z) manner trough a cross-electrophile coupling reaction. The objective of the TFG will be to optimize the reaction and to assess its generality and limitations. During the project, theoretical knowledge of organic chemistry has been reinforced and experimental skills have been developed. The bibliographic research, the synthesis of the starting materials, as well as the use of spectroscopic and chromatographic techniques, together, have allowed for the study of the reaction and the extraction of significant conclusions regarding the results obtained.