Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids

Mingfeng Yu; Joseph K-H Wong; Cyril Tang; Peter Turner; Matthew H Todd; Peter J Rutledge

doi:10.3762/bjoc.11.6

Efficient deprotection of F-BODIPY derivatives: removal of BF2 using Brønsted acids

Beilstein J Org Chem. 2015 Jan 9:11:37-41. doi: 10.3762/bjoc.11.6. eCollection 2015.

Authors

Mingfeng Yu¹, Joseph K-H Wong¹, Cyril Tang¹, Peter Turner², Matthew H Todd¹, Peter J Rutledge¹

Affiliations

¹ School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia.
² Crystal Structure Analysis Facility, School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia.

Abstract

The effective and efficient removal of the BF2 moiety from F-BODIPY derivatives has been achieved using two common Brønsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(®) 900 resin (hydroxide form) effects this conversion in near-quantitative yields. Compared to existing methods, these conditions are relatively mild and operationally simple, requiring only reaction at room temperature for six hours (TFA) or overnight (HCl).

Keywords: Brønsted acids; F-BODIPYs; click chemistry; deboration; dipyrrins.