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Use of F-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF2 Removal

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posted on 21.02.2016, 15:21 by Deborah A. Smithen, Alexander E. G. Baker, Matthew Offman, Sarah M. Crawford, T. Stanley Cameron, Alison Thompson
We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.