Journal of Organic Chemistry 2013-01-18

Conversion of F-BODIPYs to Cl-BODIPYs: enhancing the reactivity of F-BODIPYs.

Travis Lundrigan, Alison Thompson

Index: J. Org. Chem. 78(2) , 757-61, (2013)

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Abstract

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 not accessible via the direct route, as demonstrated via the use of 1,3-propanediol.