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Professor Jimmie Weaver

Organofluorine chemistry is an essential part of drug discovery programs as well as agrochemical programs and even plays a major role in materials chemistry. Despite the undeniable importance of fluorinated organic molecules, our ability to synthesize these substrates is lacking - though arguably it is better than that of Nature. Consequently, methods that allow facile access to fluorinated molecules are important especially when they provide unique access to fluorinated chemical space. One important class of these molecules are partially fluorinated arenes, i.e. Januvia. In the case of multifluorinated arenes there are two strategies to consider. The classic strategy is one in which the fluorines are systematically installed around the core of the molecule.  This strategy relies on harsh and lengthy reaction sequences such as iterative nitration, halex, reduction, Balz-Schieman. An alternative strategy is to start with a completely or nearly completely fluorinated arene and selectively functionalize or reduce the C–F bonds to build the desired molecule. This approach is ideal because many perfluoroarenes are commercially available. Furthermore, since every carbon is substituted with a fluorine it has some potential for functionalization which can allow the perfluoroarene to serve as a synthetic lynchpin. In practice, this has not yet been accomplished. The Weaver lab is actively developing strategies to achieve  this  goal.

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Sameera M Senaweera, Jimmie D Weaver
Journal of Organic Chemistry 2014-11-07
This work describes the facile and mono-selective per- and polyfluoroarylation of Meldrum's acid to generate a versatile synthon for highly fluorinated α-phenyl acetic acid derivatives, which provide straightforward access to fluorinated building blocks. The reaction takes place quickly, and most products were isolated without t...Read More
Sameera Senaweera, JimmieD Weaver
Journal of the American Chemical Society 2016-02-01
Multifluorinated biaryls are challenging to synthesize and yet are an important class of molecules. Because of the difficulty associated with selective fluorination, this class of molecules represent a formidable synthetic challenge. An alternative approach to selective fluorination of biaryls is to couple an arene that already ...Read More

 
Photocatalytic C–F alkylation; facile access to multifluorinated arenes
 
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