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Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core.

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.

SUBMITTER: Li L 

PROVIDER: S-EPMC2430868 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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Functionalization of the 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) core.

Li Lingling L   Nguyen Binh B   Burgess Kevin K  

Bioorganic & medicinal chemistry letters 20071101 10

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. ...[more]

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