Radical CH Alkylation of BODIPY Dyes Using Potassium Trifluoroborates or Boronic Acids

Author(s)

Verbelen, Bram ^[1] ; Dias Rezende, Lucas Cunha ^{[2, 1]} ; Boodts, Stijn ^[1] ; Jacobs, Jeroen ^[1] ; Van Meervelt, Luc ^[1] ; Hofkens, Johan ^[1] ; Dehaen, Wim ^[1]

Affiliation

^[1] Katholieke Univ Leuven, Dept Chem, B-3001 Louvain - Belgium

^[2] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, BR-14040903 Ribeirao Preto, SP - Brazil

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 21, n. 36, p. 12667-12675, SEP 1 2015.
• Web of Science Citations: 28

Abstract

A one-step synthetic procedure for the radical CH alkylation of BODIPY dyes has been developed. This new reaction generates alkyl radicals through the oxidation of boronic acids or potassium trifluoroborates and allows the synthesis of mono-, di-, tri-, and tetraalkylated fluorophores in a good to excellent yield for a broad range of organoboron compounds. Using this protocol, multiple bulky alkyl groups can be introduced onto the BODIPY core thus creating solid-state emissive BODIPY dyes. (AU)

• FAPESP's process: 13/24408-9 - Chemical modification of BODIPY fluorophores aiming at structural and photophysical diversity for the development of novel fluorescent probes
• Grantee: Lucas Cunha Dias de Rezende
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate