Journal
TETRAHEDRON LETTERS
Volume 54, Issue 21, Pages 2600-2603Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.03.010
Keywords
Solid-phase synthesis; Sodium dithionite; Reduction; Phase-transfer catalysis; Resin-bound nitroarene
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Funding
- Department of Chemistry and Biochemistry, University of Notre Dame
- GACR [P207/12/0473]
- European Social Fund [CZ.1.07/2.3.00/20.0009]
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Herein, conditions for the fast and effective reduction of aromatic nitro groups bound to hydrophobic polystyrene-based Wang and Ring resins utilizing sodium dithionite in dichloromethane-water under PTC conditions are reported. Tetrabutylammonium hydrogen sulfate (TBAHS) was found to be an effective phase-transfer catalyst for this reaction. This method allows for the reduction of nitro groups to amino groups under mild conditions with complete conversion and is tolerant of other functional groups. This method is a superior alternative to tin(II) chloride-based reduction, which is known for its shortcomings. (C) 2013 Elsevier Ltd. All rights reserved.
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