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Studies towards the synthesis of functionalized aryl fluorides : transition metal catalyzed cross-coupling and fluorination of organoboron reagents

University of British Columbia

This thesis covers several synthetic approaches to the generation of highly functionalized aryl fluorides. PtCl₂(SMe₂)₂ and PtCl₂(DMSO)₂ have been applied to catalytic methylation of polyfluoroaryl imines as user-friendly precatalysts. These complexes have demonstrated high selectivity for ortho C-F activation and subsequent functionalization, exhibiting high functional group tolerance while proving more thermal, moisture and air stable than our original catalyst, [PtMe₂(SMe₂)]₂. Nickel-catalyzed Suzuki-Miyaura and Negishi cross-coupling reactions allow rapid functionalized of C-F bonds; we have been able to obtain a variety of highly functionalized aryl-, heteroaryl-, and alkyl-substituted aryl fluoride molecules under mild reaction conditions. Furthermore, we have described a novel fluorination procedure that employs organoboron reagents and electrophilic fluorine sources. This method is rapid, high yielding and can be carried out without inert atmosphere protection and dry solvents.

Text

2013-01-11

Attribution-NonCommercial-NoDerivatives 4.0 International

http://hdl.handle.net/2429/43839

Chemistry

University of British Columbia

UBCV

http://creativecommons.org/licenses/by-nc-nd/4.0/