Building up molecular complexity via C-H functionalization and skeletal rearrangements

Identifier:  TDX:2507

Handle: https://hdl.handle.net/20.500.11797/TDX2507

Authors:  Gutiérrez Bonet, Alvaro

Abstract:
The construction of molecular complexity from readily available materials is of utmost importance in Organic Synthesis. In the last decades, C-H functionalization reactions have arosed as an excellent approach to such goal. The main advantages of C-H functionalization events is the no need of prefunctionalization of the substrate as well as the ubiquity of the C-H bonds. However, numerous challenges are present as well, such as the poor reactivity of these bonds and selectivity issues. During the present work, we have been able to develop two methodologies that employ C-H bonds as coupling partner with aryl halides under palladium-catalysis for the construction of benzofused bucyclic systems of high added value: Benzocyclobutenones and indanes. In the first case, an aldehydic C(sp2)-H bond is activated for the synthesis of a highly strained four-membered ring. For the second, diazo compounds are combined with non-activated C(sp3)-H bonds for the synthesis of indanyl-cores bearing two quaternary centers.