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Lewis Acid Assisted Decomplexation of F‐BODIPYs to Dipyrrins
Author(s) -
Lakshmi Vellanki,
Chatterjee Tamal,
Ravikanth Mangalampalli
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301662
Subject(s) - chemistry , lewis acids and bases , steric effects , boron , aryl , fluorine , boronic acid , medicinal chemistry , boron trifluoride , combinatorial chemistry , organic chemistry , catalysis , alkyl
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 ZrCl 4 , TiCl 4 , AlCl 3 , Sc(OTf) 3 , or SnCl 4 in CH 3 CN/CH 3 OH 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 BF 2 complex of 25‐oxasmaragdyrin.