Literature DB >> 24849815

Activation and deprotection of F-BODIPYs using boron trihalides.

Travis Lundrigan1, T Stanley Cameron, Alison Thompson.   

Abstract

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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Year:  2014        PMID: 24849815     DOI: 10.1039/c4cc02706j

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  6 in total

1.  Development of a multi faceted platform containing a tetrazine, fluorophore and chelator: synthesis, characterization, radiolabeling, and immuno-SPECT imaging.

Authors:  Anthony W McDonagh; Brooke L McNeil; Julie Rousseau; Ryan J Roberts; Helen Merkens; Hua Yang; François Bénard; Caterina F Ramogida
Journal:  EJNMMI Radiopharm Chem       Date:  2022-06-06

2.  Benzene-fused bis(acenaphthoBODIPY)s, stable near-infrared-selective dyes.

Authors:  Hidemitsu Uno; Takayuki Honda; Manami Kitatsuka; Shogo Hiraoka; Shigeki Mori; Masayoshi Takase; Tetsuo Okujima; Takahiro Nakae
Journal:  RSC Adv       Date:  2018-04-16       Impact factor: 4.036

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

Authors:  Mingfeng Yu; Joseph K-H Wong; Cyril Tang; Peter Turner; Matthew H Todd; Peter J Rutledge
Journal:  Beilstein J Org Chem       Date:  2015-01-09       Impact factor: 2.883

4.  Stability of a Series of BODIPYs in Acidic Conditions: An Experimental and Computational Study into the Role of the Substituents at Boron.

Authors:  Maodie Wang; M Graça H Vicente; Deanna Mason; Petia Bobadova-Parvanova
Journal:  ACS Omega       Date:  2018-05-21

5.  Facile deprotection of F-BODIPYs using methylboronic acid.

Authors:  Craig D Smith; Alison Thompson
Journal:  RSC Adv       Date:  2020-06-25       Impact factor: 4.036

6.  Facile Arylation of Four-Coordinate Boron Halides by Borenium Cation Mediated Boro-desilylation and -destannylation.

Authors:  Daniel L Crossley; Jessica Cid; Liam D Curless; Michael L Turner; Michael J Ingleson
Journal:  Organometallics       Date:  2015-12-08       Impact factor: 3.876

  6 in total

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