Literature DB >> 22356438

Use of F-BODIPYs as a protection strategy for dipyrrins: optimization of BF(2) removal.

Deborah A Smithen1, Alexander E G Baker, Matthew Offman, Sarah M Crawford, T Stanley Cameron, Alison Thompson.   

Abstract

We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF(2) moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF(2)-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.

Entities:  

Year:  2012        PMID： 22356438     DOI： 10.1021/jo3002003

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  8 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.  Shedding light on the mitochondrial matrix through a functional membrane transporter.

Authors:  Alberto Blázquez-Moraleja; Ines Sáenz-de-Santa María; María D Chiara; Delia Álvarez-Fernández; Inmaculada García-Moreno; Ruth Prieto-Montero; Virginia Martínez-Martínez; Iñigo López Arbeloa; Jose Luis Chiara
Journal:  Chem Sci       Date:  2019-12-09       Impact factor: 9.825

4.  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

5.  Synthesis of Functional Fluorescent BODIPY-based Dyes through Electrophilic Aromatic Substitution: Straightforward Approach towards Customized Fluorescent Probes.

Authors:  Giorgio Mirri; Daniël C Schoenmakers; Paul H J Kouwer; Peter Veranič; Igor Muševič; Bogdan Štefane
Journal:  ChemistryOpen       Date:  2016-08-19       Impact factor: 2.911

6.  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

7.  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

8.  Prodigiosin analogue designed for metal coordination: stable zinc and copper pyrrolyldipyrrins.

Authors:  Tsuhen M Chang; Sanhita Sinharay; Andrei V Astashkin; Elisa Tomat
Journal:  Inorg Chem       Date:  2014-07-10       Impact factor: 5.165
  8 in total

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