An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis(dipyrrin)s

Lundrigan, Travis; E. G. Baker, Alexander; Longobardi, Lauren E.; Wood, Tabitha E.; Smithen, Deborah A.; Crawford, Sarah M.; Cameron, T. Stanley; Thompson, Alison

doi:10.1021/ol300681w.s001

ol300681w_si_001.pdf (10.24 MB)

An Improved Method for the Synthesis of F-BODIPYs from Dipyrrins and Bis(dipyrrin)s

journal contribution

posted on 2012-04-20, 00:00 authored by Travis Lundrigan, Alexander E. G. Baker, Lauren E. Longobardi, Tabitha E. Wood, Deborah A. Smithen, Sarah M. Crawford, T. Stanley Cameron, Alison Thompson

An improved methodology for the synthesis of F-BODIPYs from dipyrrins and bis(dipyrrin)s is reported. This strategy employs lithium salts of dipyrrins as intermediates that are then treated with only 1 equiv of boron trifluoride diethyletherate to obtain the corresponding F-BODIPYs. This scalable route to F-BODIPYs renders high yields with a facile purification process involving merely filtration of the reaction mixture through Celite in many cases.