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

Beilstein Journal of Organic Chemistry (Jan 2015)

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

Affiliations

Mingfeng Yu: School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia
Joseph K.-H. Wong: School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia
Cyril Tang: School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia
Peter Turner: Crystal Structure Analysis Facility, School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia
Matthew H. Todd: School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia
Peter J. Rutledge: School of Chemistry, The University of Sydney, Sydney, New South Wales 2006, Australia

DOI: https://doi.org/10.3762/bjoc.11.6
Journal volume & issue: Vol. 11, no. 1
pp. 37 – 41

Abstract

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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).

Published in Beilstein Journal of Organic Chemistry

ISSN: 1860-5397 (Online)
Publisher: Beilstein-Institut
Country of publisher: Germany
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.beilstein-journals.org/bjoc

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