Lewis acid assisted decomplexation of F-BODIPYs to dipyrrins

Lakshmi, Vellanki ; Chatterjee, Tamal ; Ravikanth, Mangalampalli (2014) Lewis acid assisted decomplexation of F-BODIPYs to dipyrrins European Journal of Organic Chemistry, 2014 (10). pp. 2105-2110. ISSN 1434-193X

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...

Related URL: http://dx.doi.org/10.1002/ejoc.201301662

Abstract

A simple synthetic route was developed for the decomplexation of F-BODIPYs (fluorine-substituted boron–dipyrromethenes) to afford dipyrrins in high yields. This was achieved by treating the F-BODIPYs with different Lewis acids such as ZrCl4, TiCl4, AlCl3, Sc(OTf)3 or SnCl4 in CH3CN/CH3OH under refluxing conditions. This synthetic strategy was efficient for different types of F-BODIPYs such as meso-aryl-substituted BODIPYs, 3-pyrrolyl BODIPYs, functionalized 3-pyrrolyl BODIPYs, π-extended pyrrolyl BODIPYs, sterically crowded BODIPYs and the BF2 complex of 25-oxasmaragdyrin.

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