4.5 Article

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

期刊

出版社

BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.11.6

关键词

Bronsted acids; click chemistry; deboration; dipyrrins; F-BODIPYs

资金

  1. National Breast Cancer Foundation for a Novel Concept Grant [NC-10-69]
  2. Australian Research Council [DP120104035]
  3. University of Sydney International Scholarship (USydIS)
  4. Australian Postgraduate Award (APA) from the Australian Government

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The effective and efficient removal of the BF2 moiety from F-BODIPY derivatives has been achieved using two common Bronsted acids; treatment with trifluoroacetic acid (TFA) or methanolic hydrogen chloride (HCl) followed by work-up with Ambersep(R) 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).

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