Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF(2) removal.
Deborah A Smithen, Alexander E G Baker, Matthew Offman, Sarah M Crawford, T Stanley Cameron, Alison Thompson
Department of Chemistry, Dalhousie University, P.O. Box 15000, Halifax, Nova Scotia, Canada.
The Journal of organic chemistry 2012 Apr 6We 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.
Citation
Deborah A Smithen, Alexander E G Baker, Matthew Offman, Sarah M Crawford, T Stanley Cameron, Alison Thompson. Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF(2) removal. The Journal of organic chemistry. 2012 Apr 6;77(7):3439-53
PMID: 22356438
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