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Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF(2) removal
Deborah A Smithen1, Alexander E G Baker, Matthew Offman
1Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, Nova Scotia, Canada.
Abstract:
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 BF(2) 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 BF(2)-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.
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