Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core.
The new BODIPY systems 1 and 2 were prepared and then used as substrates to explore S(N)Ar and F-B displacement reactions. Chloride was easily displaced from 1 by a piperidine/ester, methylmagnesium bromide selectively displaced fluoride, and cyanide could attack both sites. System 2 readily added soft nucleophiles to the electrophilic carbon atoms, providing a new method for bioconjugation of BODIPYs to proteins while also introducing a (19)F probe.
Department of Chemistry, Texas A&M University, Box 30012, College Station, TX 77842-3012, USA.
Lingling
L
Li
Binh
B
Nguyen
Kevin
K
Burgess
D001896:Boron Compounds / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry; D017616:Magnesium Compounds / Q000737:chemistry; D015335:Molecular Probes / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D002712:Chlorides; D003486:Cyanides; D005456:Fluorescent Dyes; D017616:Magnesium Compounds; D015335:Molecular Probes; D010880:Piperidines; D005459:Fluorides