8-Halogenated boradiaza-s-indacenes can be efficiently prepared from dipyrrylketones. The new dyes react smoothly with nucleophiles to yield N-, O-, and S-substituted chromophores, as well as transition-metal-catalyzed cross-coupling reactions. The nature of the new substitutent has a strong influence on the spectral properties of the dyes.
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Synthesis of meso-halogenated BODIPYs and access to meso-substituted analogues.
Org Lett
December 2012
Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200f-bus 02404, 3001 Leuven, Belgium.
8-Halogenated boradiaza-s-indacenes can be efficiently prepared from dipyrrylketones. The new dyes react smoothly with nucleophiles to yield N-, O-, and S-substituted chromophores, as well as transition-metal-catalyzed cross-coupling reactions. The nature of the new substitutent has a strong influence on the spectral properties of the dyes.
View Article and Find Full Text PDFVersatile synthesis of meso-aryloxy- and alkoxy-substituted porphyrins via palladium-catalyzed C-O cross-coupling reactions.
Org Lett
September 2003
Department of Chemistry, University of Tennessee, Knoxville, Tennessee 37996-1600, USA.
[reaction: see text] meso-Aryloxy- and alkoxy-substituted porphyrins were conveniently synthesized by direct reactions of meso-halogenated porphyrins with alcohols via palladium-catalyzed C-O cross-coupling reactions. Using a combination of palladium precursor Pd(OAc)(2) or Pd(2)(dba)(3) and phosphine ligand DPEphos or Xantphos allowed both 5-bromo-10,20-diarylporphyrin and 5,15-dibromo-10,20-diarylporphyrin, as well as their zinc complexes, to be effectively coupled with a variety of alcohols to give the corresponding mono- and bis-substituted meso-aryloxy/alkoxyporphyrins in moderate to high yields under mild conditions.
View Article and Find Full Text PDFFacile and efficient synthesis of meso-arylamino- and alkylamino-substituted porphyrins via palladium-catalyzed amination.
J Org Chem
May 2003
Department of Chemistry, University of Tennessee, Knoxville 37996-1600, USA.
meso-Arylamino- and alkylamino-substituted porphyrins were efficiently synthesized by reactions of meso-halogenated porphyrins with amines via palladium-catalyzed amination. The combination of palladium acetate and the commercially available phosphine ligand bis(2-diphenylphosphinophenyl) ether (DPEphos) is effective for catalyzing the couplings of both [5-bromo-10,20-diphenyl porphyrino]zinc(II) and [5,15-dibromo-10,20-diphenylporphyrino]zinc(II) with amines to give the corresponding monoamino- and diamino-substituted porphyrins in high yields under mild conditions. The corresponding halogenated free-base porphyrins also underwent the cross-coupling reactions efficiently under similar catalytic conditions.
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