Birch Reduction of Arenes Using Sodium Dispersion and DMI under Mild Conditions
- 7 October 2021
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 51 (1), 38-40
- https://doi.org/10.1246/cl.210546
Abstract
An easy-to-handle sodium dispersion in paraffin oil (SD), in combination with inexpensive and environmentally benign 1,3-dimethyl-2-imidazolidinone (DMI) as an additive enables the Birch-type reduction of a variety of arenes with high yields, selectivity, and tolerance of functionality such as ether, alcohol, amine, amide, and carboxylic acid.Keywords
This publication has 66 references indexed in Scilit:
- A Mechanistic Analysis of the Birch ReductionAccounts of Chemical Research, 2011
- Electroreduction of aromatics using magnesium electrodes in aprotic solvents containing alcoholic proton donorsElectrochimica Acta, 2003
- Birch reduction and its application in the total synthesis of natural productsPure and Applied Chemistry, 2003
- Synthesis and structures of two thermally stable sodides with the macrocyclic complexant hexamethyl hexacyclenJournal of the American Chemical Society, 1989
- Structure of K+(cryptand[2.2.2J) electride and evidence for trapped electron pairsNature, 1988
- Recent developments in the synthesis of alkalides and electridesThe Journal of Physical Chemistry, 1984
- N.m.r. spectrum of Na–in sodium–hexamethylphosphoric triamide solutionsJournal of the Chemical Society, Chemical Communications, 1981
- Cyclotrimerization of 2-butyne-1,1,1-d3 by transition metal catalystsJournal of the American Chemical Society, 1969
- Reduction of Organic Compounds by Lithium in Low Molecular Weight Amines. I. Selective Reduction of Aromatic Hydrocarbons to MonoölefinsJournal of the American Chemical Society, 1955
- The True Identity of the Solvated Free Radical “Triphenylsilicyl Ethylammine.” The Multiple Addition of Lithium to an Aromatic System in EthylamineJournal of the American Chemical Society, 1952