Nucleophilic Substitution on (Pentafluorophenyl)dipyrromethane: A New Route to Building Blocks for Functionalized BODIPYs and Tetrapyrroles

The reaction of alcohols with (pentafluorophenyl)dipyrromethane (PFP-DPM) under basic conditions has been studied, giving access to the corresponding alkoxy-substituted DPMs. This method represents the first high-yielding substitution of PFP-DPM carried out with oxygen nucleophiles. Condensation of...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2015-02, Vol.17 (4), p.982-985
Main Authors: Golf, Hartwig R. A, Reissig, Hans-Ulrich, Wiehe, Arno
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reaction of alcohols with (pentafluorophenyl)dipyrromethane (PFP-DPM) under basic conditions has been studied, giving access to the corresponding alkoxy-substituted DPMs. This method represents the first high-yielding substitution of PFP-DPM carried out with oxygen nucleophiles. Condensation of these prefunctionalized DPMs with aldehydes led to the respective trans-A2B2 porphyrins. This pathway allows a simple synthesis of multifunctionalized tetrapyrroles. Oxidation and boron complexation of these DPMs, on the other hand, led to meso-functionalized difluoroboraindacenes (BODIPYs). In addition, nucleophilic substitution of PFP-BODIPY with sodium azide led to a 4-azidophenyl derivative, thus further enhancing the scope of reactive sites suitable for subsequent transformations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b00082