Facile deprotection of F-BODIPYs using methylboronic acid

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Activation and deprotection of F-BODIPYs using boron trihalides.

The activation of F-BODIPYs with boron trihalides, followed by treatment with a nucleophile, effects facile substitution at boron; using water as the nucleophile promotes deprotective removal of the -BF2 moiety and thereby production of the corresponding parent dipyrrin salt in quantitative yield under extremely mild conditions.

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A new method for the synthesis of Cl-BODIPYs from F-BODIPYs is reported, merely requiring treatment of the F-BODIPY with boron trichloride. Cl-BODIPYs are exploited as synthetic intermediates generated in situ for the overall conversion of F-BODIPYs to O- and C-BODIPYs in high overall yields using a mild one-pot procedure. This route enables F-BODIPYs to be transformed into derivatives that are...

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Cl-BODIPYs: a BODIPY class enabling facile B-substitution.

Cl-BODIPYs, synthesized in high yields from dipyrrins under air- and moisture-free conditions, are extremely facile to substitution at boron compared to their corresponding F-BODIPYs, opening up a new route to BODIPYs functionalized at boron.

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ژورنال

عنوان ژورنال: RSC Advances

سال: 2020

ISSN: 2046-2069

DOI: 10.1039/d0ra05151a