metaC-Hfunct · CO2 as a traceless directing group for catalytic meta C-H olefinations
Horizon 2020 — Marie Skłodowska-Curie Actions
- Duration
- 2015-04-01 → 2017-03-31
- EU contribution
- €183,455
- Participants
- 1
- Scheme
- MSCA-IF-EF-ST
Lines connect the coordinator with its partners.
Results in brief
CO2 as a traceless directing group for catalytic meta C-H olefinations
The objectives of this project are in line with the development of meta-functionalized fluoroarenes and other substituted arenes from their corresponding arene precursors via C–H bond functionalization. Fluorinated biaryl motifs are a particularly important class within fluorinated compounds, with widespread presence in pharmaceuticals and agrochemicals. The methods currently utilized to access fluorinated arene motifs suffer from major drawbacks such as the need to use prefunctionalized molecules that either have elevated costs or require synthetic steps for their preparation and also lead to the generation of significant amounts of waste. The project we have developed allows for the use of inexpensive and readily available fluoroarenes as precursors for the synthesis of fluorinated biaryl motifs leading to greener and faster protocols towards such motifs. This project also contributes to create accelerated synthetic routes towards compounds with pharmaceutical and agrochemical interest.
Data: CORDIS, © European Union
Project objective
The development of methods for the transition metal-catalysed functionalization of C-H bonds is revolutionizing synthetic organic chemistry by providing tools to simplify and accelerate the synthesis and modification of a myriad of known and still unknown organic molecules including aromatic compounds. However, in these processes, the ability to discriminate between C-H bonds for subsequent transformation into other functional groups still remains as a major challenge. To date, much progress has been made on developing strategies for the ortho-functionalization of arenes, mainly through the derivatization of the substrates with directing groups. meta-Functionalization approaches, on the other hand, are extremely scarce despite eta-substitution is a widespread motive amongst biologically active molecules. The research outlined in this proposal aims at developing a process that makes use of CO2 as an invisible directing group leading to an array of novel direct meta-functionalization methodologies. To do so, we envision a one-pot strategy involving a carboxylation ortho to an R group followed by a tandem CO2H directed ortho-functionalization/decarboxylation process that affords the desired meta-functionalized products and releases again the CO2 employed as the directing group.The realisation of the objectives of this project will push forward the state-of-the art in the area of C-H bond activation by providing step economical access to molecules that are difficult to prepare via conventional multistep routes.
Original text from CORDIS.
Participants
- THE UNIVERSITY OF MANCHESTER · ManchesterCoordinatorUnited Kingdom
Links
Data: CORDIS, © European Union