Abstract
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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Boron Compounds / chemistry*
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Chlorides / chemistry
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Cyanides / chemistry
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Fluorescent Dyes / chemical synthesis*
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Fluorescent Dyes / chemistry*
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Fluorides / chemistry
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Magnesium Compounds / chemistry
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Molecular Probes / chemistry*
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Molecular Structure
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Piperidines / chemistry
Substances
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4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
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Boron Compounds
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Chlorides
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Cyanides
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Fluorescent Dyes
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Magnesium Compounds
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Molecular Probes
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Piperidines
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Fluorides