Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal.
Smithen, Deborah A.
Baker, Alexander E. G.
Crawford, Sarah M.
Cameron, T. Stanley
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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.
Smithen, D. A., Baker, A. E., Offman, M., Crawford, S. M., Cameron, T. S., & Thompson, A. (2012). Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF2 removal. The Journal of organic chemistry, 77(7), 3439-3453. DOI: 10.1021/jo3002003